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CAS No. : | 92-44-4 | MDL No. : | MFCD00004073 |
Formula : | C10H8O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JRNGUTKWMSBIBF-UHFFFAOYSA-N |
M.W : | 160.17 | Pubchem ID : | 7091 |
Synonyms : |
2,3-Naphthalenediol
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 47.99 |
TPSA : | 40.46 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.69 cm/s |
Log Po/w (iLOGP) : | 1.47 |
Log Po/w (XLOGP3) : | 2.24 |
Log Po/w (WLOGP) : | 2.25 |
Log Po/w (MLOGP) : | 1.88 |
Log Po/w (SILICOS-IT) : | 2.01 |
Consensus Log Po/w : | 1.97 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.86 |
Solubility : | 0.221 mg/ml ; 0.00138 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.73 |
Solubility : | 0.301 mg/ml ; 0.00188 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.91 |
Solubility : | 0.197 mg/ml ; 0.00123 mol/l |
Class : | Soluble |
PAINS : | 1.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With potassium carbonate In acetone Inert atmosphere; | |
72% | Stage #1: 2,3-naphthalenediol With potassium carbonate In acetone at 25℃; for 0.166667h; Stage #2: allyl bromide In acetone | 10 2.1.6 Synthesis of 7-(allyloxy)naphthalen-2-ol General procedure: 2,7-Dihydroxynaphthalene (800 mg, 5.0 mmol) was dissolved in acetone (15 mL) followed by the addition of K2CO3 (759 mg, 5.5 mmol) at 25 °C. After stirring for 10 min, allyl bromide (475 μL, 5.5 mmol) was added dropwise to the solution mixture. The mixture was allowed to stir for an overnight. TLC indicated the disappearance of the starting material. The mixture was then filtered through a small pad of silica gel, which was further washed with dichloromethane. After that, the collected filtrate was concentrated and purified by column chromatography to give the product as colorless oil (346 mg, 1.7 mmol). Yield: 34%; Rf = 0.5 (EtOAc/n-hexanes, 1:6); 1H NMR (CDCl3, 400 MHz) δ 4.63 (d, J = 5.3 Hz, 2H), 5.13 (brs, 1H), 5.32 (dd, J = 0.9, 10.5 Hz, 1H), 5.47 (dd, J = 1.3, 17.3 Hz, 1H), 6.07-6.17 (m, 1H), 6.94 (dd, J = 2.4, 8.8 Hz, 1H), 6.98-7.04 (m, 3H), 7.66 (d, J = 8.8 Hz, 2H); 13C NMR (CDCl3, 100 MHz) δ 68.9, 106.0, 108.9, 115.4, 116.7, 118.0, 124.5, 129.4, 129.7, 133.3, 136.0, 154.1, 157.3; HRMS (ESI) m/z Calc. for C13H12O2 [M+H]+ 201.0910. Found: 201.0913.1.8 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium carbonate; In acetone; for 12h;Reflux; | 2,3-dinaphthol (5 g, 31.25 mmol) was dissolved in 75 mL of acetone, K2CO3 (9.5 g, 68.75 mmol) was added,And then droppingDimethyl sulfate (6.65 mL, 68.75 mmol), refluxed for 12 hours, cooled,Acetone was washed and concentrated to give 2,3-dimethoxynaphthalene in 90% yield. |
70% | With potassium hydroxide; In water; at 20℃; | A suspension of 2,3-dihydroxynaphthalene [(5.] 00g, 0.0312 mol) in water (25 mL) in a three-necked round-bottomed flask was cooled in an ice-bath. Two pressure equilibrating funnels were set up and these charged with dimethyl sulphate (7.20 mL, 9.57 g, 0.0759 mol) and aqueous potassium hydroxide (5.57 g, 0.0993 mol in 17.0 mL of water) respectively. Both of these were added together dropwise over 10 minutes resulting in the suspension first dissolving and then a precipitate forming. The reaction was left overnight at room temperature. The solid was then filtered off, washed with water until the washings were neutral (5 x 200 mL), and dried to give 2,3-dimethoxynaphthalene (4.09 g, 70% yield) as a white powder; Rf:0. 71 (19: 1 [CHCL3] : MeOH), 0.82 (9: 1 [CHCL3] : MeOH), mp: [112-113 C,] lit. mp: [L 13-116C] ; [IH] NMR (CDCl3/TMS) : [6] 4.01 (s, 6 H, 2 x OCH3), 7.13 (s, 2H), 7.33-7. 36 (m, 2H), 7.68- 7.71 (m, 2H); LRESI mass spectrum: [M/Z] 189 (100%, MH+). |
> 90 kg | With potassium carbonate; In acetone; at 20 - 60℃; for 6h;Large scale; | Preparation of Compound 4: Acetone (850 L), 2,3-dihydroxynaphthalene (85.00 kg, 530.7 moles), and potassium carbonate (219.3 kg, 1,586.7 moles) were charged to a clean, fixed reactor with stirring and with the temperature maintained at 20 - 35 C. Dimethyl sulfate (200.6 kg, 2131.09) was added to the stirred reaction at a rate that maintains the internal temperature of the exothermic reaction below 60 C. This addition typically requires about 3 hours. At the end of the dimethyl sulfate addition, the reaction is continued to allow to stir while maintaining the internal temperature at 50 - 60 C. After about 3 hours, the reaction was analyzed by HPLC. The reaction was concentrated by atmospheric pressure distillation of acetone. The distillation was continued until 340 - 425 L of distillate was collected. This represents 40 - 50 % of the initial charge of acetone. At the end of the distillation, the reaction mass is present as a thick suspension. While maintaining the internal temperature below 60 C, the reactor contents were slowly diluted with water (850 L). When the addition is complete, the reaction was cooled to an internal temperature of 25 - 35 C and stirring was continued for 1 - 2 hours after the designated internal temperature was reached. Compound 2 was isolated by filtration and the cake was washed with water (at least 3 X 85 L). Compound 2 was dried at 40 - 45 C and full vacuum until the water content by Karl Fisher titration is found to be NMT 2.0 %. Typically, greater than 90 kg of dry product is obtained with an assay of >99.5% AUC by HPLC. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In water; | (a) 3-Methoxy-naphthalen-2-ol Dimethylsulfate (32 ml) was added to the solution of 2,3-dihydroxynaphthalene (32 g) and sodium hydroxide (10 M, 32 ml) in water (300 ml). After being stirred for six hours at room temperature, the side product 2,3-dimethoxynaphthalene was filtered off (yield 16.6 g). The water phase was acidified, stirred on ice bath, filtered, washed with water and recrystallized from ethanol-water (3:2). Yield: 13.5 g, melting point 108-109 C. 1H-NMR (DMSO-d6): 9.47 (b,1H), 7.69-7.71 (m,1H), 7.60-7.62 (m,1H), 7.22-7.27 (m,3H), 7.14 (s,1H),3.90 (s,3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With iron(III) chloride at 50℃; for 1h; Irradiation; solid state; | |
89% | With iron(III) chloride at 50℃; for 1h; Irradiation; | |
75% | With Cu(II) oxymetasilicate for 0.05h; microwave irradiation; |
70% | With potassium peroxodisulfate In trifluoroacetic acid at 20℃; for 16h; Sealed tube; Schlenk technique; regioselective reaction; | |
66% | at 100℃; for 0.25h; | |
53% | Stage #1: 2,3-naphthalenediol With iron(III) trichloride hexahydrate at 50℃; for 1h; ultrasound irradiation; Stage #2: With hydrogenchloride In water monomer | 2 A literature procedure was employed [Toda 1989]. A mixture of 2,3-naphthalenediol (16 g, 0.1 mol) and FeCI3-6H2O (27 g, 0.2 mol) was finely powdered by agate mortar and pestle. The mixture was then put in a test tube and irradiated with ultrasound at 5O0C for 1 h. Decomposition of the reaction mixture with dilute HCI gave crude 2, 2'3,3'-tetrahydroxy-1 ,1 '-dinaphthyl in 85% yield. The tetrol was recrystallized from THF three times to give white needle powder at 53% yield. Mp > 3000C.1H NMR (DMSO-d6) δ 6.80-6.82 (d, J = 8.0 Hz, 2H), 6.94-6.98 (t, J = 8.0 Hz, 2H), 7.14-7.18 (t J = 8.0 Hz, 2H), 7.24 (s, 2H), 7.64-7.62 (d, J = 8.0 Hz, 2H), 8.41 (s, OH), 10.07 (S1 OH)Elem. Anal. Calcd for C20H14O4 (318.32 g/mol): C, 75.46%; H, 4.43% Found: C, 75.41%; H, 4.56%. |
53% | With ferric chloride hexahydrate at 50℃; for 4h; Sonication; | |
50% | With 3-methylbenzo[b]thiophene; dihydrogen peroxide; trifluoroacetic acid; trifluoroacetic anhydride In dichloromethane; water monomer at 0 - 20℃; for 2h; Inert atmosphere; | |
With ferric ammonium sulfate | ||
With potassium periodate In methanol; water monomer other solvents; | ||
With iron(III) chloride; magnesium(II) bromide 2) CH3NO2, 25 deg C, 5 h; Yield given. Multistep reaction; | ||
With iron(III) trichloride hexahydrate at 50℃; for 4h; Sonication; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With triethylamine In chloroform at 0℃; | 2,3-Bis(methylsulfonyloxy)naphthalene MsCl (39.3 g, 26.5 mL, 0.343 mol) was added to a solution of 2,3-dihydroxynaphthalene (3) (25 g, 0.156mol), Et3N (34.7 g, 47.9 mL, 0.343 mol) in CHCl3 (500 mL) at 0 °C, then the mixture was allowed tostand at rt. After the resulting precipitates were removed by filtration, water was added to the motherliquid which was extracted with CHCl3. The organic layer was washed with brine, dried oved MgSO4,and concentrated to give a crude residue. Recrystallization from CHCl3 gave 4 (48.8 g, 99%) in almost apure form. Colorless needles, mp 153.9157.2 °C (CHCl3) [lit.11 159-160 °C]. IR (KBr) cm-1: 1360, 1180.1H-NMR (300MHz, CDCl3) δ: 3.29 (6H, s, CH3), 7.587.95 (6H, m, Ar-H). |
96% | With triethylamine In dichloromethane for 2h; | 3.a a. Preparation of CompoundA solution of 5.0 g of 2, 3-dihydroxynaphthalene in 50 ml of dichloromethane and 20 ml of triethylamine was treated drop-wise with 10 ml of methanesulfonyl chloride. After stirring for two hours, the white precipitate was collected by filtration and washed with ethanol to yield the 2, 3-dihydroxynaphthalene dimesitylate as colorless solid. (Yield = 9.5 g (96%) . mp 160- 1630C. 1H NMR (DMSO-d6) δ 3.53 (s, 6H), 7.80 (m, 5H), 8.10 (s, IH) .) |
88% | With triethylamine In ethyl acetate at 0 - 20℃; for 0.166667h; Green chemistry; | 3. General Procedure for the Synthesis of Aryl Mesylates (Table 4) General procedure: To a solution of hydroxyarene (25.0 mmol) in ethyl acetate (75 mL) at 0 °C was added triethylamine (5.06 g, 50.0 mmol) followed by MsCl (3.72 g, 32.5 mmol). After addition of MsCl, the ice-water bath was removed and the resulting thick slurry was vigorously stirred for 10 min. To the slurry was then added water (50 mL). The two-phase mixture was separated. The organic layer was washed with water (25 mL) and dried over anhydrous MgSO4. Removal of solvent under reduced pressure gave the corresponding pure aryl mesylate. |
67% | In pyridine for 4h; Ambient temperature; | |
With triethylamine In chloroform | ||
With triethylamine In chloroform at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: 2,3-naphthalenediol With caesium carbonate In N,N-dimethyl-formamide for 0.25h; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; for 5h; | Preparation of terminal diyne Naphthalene-2,3-diol (1.0 mmol) was dissolved in dry DMF (3 mL) and then Cs2CO3 (2.4mmol) was added. After 15 min, 3-bromoprop-1-yne (2.6 mmol) was added at room temperature. The reaction was monitored by TLC, and after completion (5 h), the mixture was diluted with ethyl acetate and washed three times with brine, to completely remove DMF. After workup, the solvent was removed under reduced pressure. The solid residue was purified by flash chromatography [SiO2, petroleum ether/ethyl acetate (30:1)] to give the product of terminal diyne (white solid, yield 88%). |
With potassium carbonate In acetone Heating; | ||
With potassium carbonate 1.) acetone; other reagent: sodium hydride, 2.) acetone, reflux; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With 2,6-dimethylpyridine In dichloromethane at 25℃; for 3h; | |
90% | With triethylamine In dichloromethane at -78 - 20℃; | |
89% | Stage #1: 2,3-naphthalenediol With triethylamine In dichloromethane at -78 - 20℃; for 2h; Schlenk technique; Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at -78 - 20℃; Schlenk technique; |
88% | With triethylamine In dichloromethane at -78 - 25℃; Inert atmosphere; | Naphthalene-2,3-diyl bis(trifluoromethanesulfonate)3 (S18) To a solution of naphthalene-2,3-diol (1.0 g, 6.24 mmol) in DCM (20 mL) under argon wasadded Et3N (3.45 mL, 25 mmol). The mixture was cooled down to -78 °C and Tf2O (2.3 mL,13.7 mmol) was added dropwise. After 7 min, the reaction mixture warmed up to roomtemperature. After 20 min, the reaction mixture was diluted with 10% HCl (20 mL) andextracted with DCM (2x20 mL), washed with saturated NaHCO3 (50 mL), brine (50 mL), dried(MgSO4), filtered and evaporated under reduced pressure. The crude product was purified byflash chromatography on silica gel (5% EtOAc/pentane) to give the title compound S18 (2.3 g,88%). |
80% | With triethylamine In dichloromethane at 0 - 20℃; for 5h; | 1 Synthesis of Intermediate 2-1 In a flask in which 1.60 g of Naphthalene-2,3-diol (10 mmol) and 4.18 mL of triethylamine (30 mmol) are dissolved in 60 mL of DCM,3.36ml of Trifluoromethanesulfonicanhydride (20mmol) was dissolved in 20ml of DCM, then slowly added at 0°C and stirred at room temperature for 5 hours. 40 mL of water was added to the reaction solution and extracted three times with 50 mL of ether. After the aggregated organic layer was dried with MgSO4, the solvent was evaporated, and the obtained residue was separated and purified by silica gel column chromatography to obtain 3.58 g of Intermediate 2-1 (yield 80%) |
78% | With triethylamine In dichloromethane at -20 - 20℃; | |
69.6% | With pyridine at 20℃; for 2h; Cooling with ice; | 7 Synthesis of 23NpOTf2 2,3-dihydroxynaphthalene 5.00g (31.2mmol, 1.0eq.) Was dissolved in pyridine 80 mL, under cooling with ice trifluoromethylsulfonate anhydride 12.6 mL (74.9 mmol, 2.4eq.) was dropped slowly.After stirring for 1 hour under ice-cooling, and the mixture was stirred at room temperature for 1 hour.Water was added, then extracted 3 times with toluene, summarized toluene layer was dried over anhydrous sodium sulfate.Aftersodium sulfate, concentrated, toluene - heptane: through silica gel column chromatography (1: 4 (volume ratio)) as eluent.The fractions containing the desired product was collected, and concentrated to give, to obtain the desired product "23NpOTf2" as a white solid (yield: 9.23g, yield: 69.6%, purity: 99.8% (HPLC)) . |
With pyridine 1.) 0 deg C, 5 min, 2.) 0 deg C to r.t., 24 h; Yield given; | ||
29.6 g | With pyridine In dichloromethane at 0 - 20℃; for 14h; | 1.1.1 1) Synthesis of intermediate I-2 2,3-Dihydroxynaphthalene (16 g), pyridine (7.9 mL) and dichloromethane (64 mL) were added to a 250 mL three-neck round bottom flask and the temperature of the reaction solution was lowered to 0 with stirring. Trifluoromethanesulfonic anhydride (31 g) was slowly added dropwise to the reaction solution. After stirring at the same temperature for 2 hours, the reaction solution was slowly raised to room temperature and stirred for 12 hours. The resulting material was purified by silica gel column chromatography (eluent: n-hexane: ethyl acetate = 5: 1) to give the title compound as a colorless oil. , And then recrystallized with n-hexane / diethyl ether to obtain 29.6 g of a dark brown solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With potassium ethoxide In ethanol Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With potassium carbonate; In N,N-dimethyl-formamide; at -5 - 20℃; for 0.5h;Inert atmosphere; | EXAMPLES 1 and 2To a stirred solution of 2,3-dihydroxy-naphthalene (10.0 g, 0.06 mol) in DMF (100 mL) was added K2CO3 (45.6 g, 0.33 mol) portion wise at room temperature under N2 atmosphere. The reaction mixture was then cooled to 0 C to -5 C, methyl iodide (28 g, 0.19 mol) was added drop wise over a period of 30 min at same temperature. After completion of addition, the reaction mixture was allowed to warm to room temperature and stirred for 16 h at RT. The reaction mixture was quenched with cold water and stirred for 20 min. The precipitated solid was filtered, washed with water (2 x 50 mL) and dried under vacuum to obtain D (8.0 g, 69%) as white solid. 1H NMR (200 MHz, CDC13): ? 7.71-7.66 (m, 2 H), 7.35-7.31 (m, 2 H), 7.12 (s, 2 H), 4.0 (s, 6 H). MS (ESI): m/z 189 [M++l]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 78 percent / NEt3 / CH2Cl2 / -20 - 20 °C 2: 85 percent / Pd2(dba)3, dppf / dimethylformamide / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With guanidine hydrochloride In neat (no solvent) at 100℃; for 1h; Green chemistry; | General procedure for the synthesis of benzo[f]chromens4a-fand 12H-benzo[5,6]chromeno[2,3-b]pyridines 9a-f General procedure: In a 25 mL round bottom flask, a mixture of 2,3-dihydroxynaphthalene (1 mmol),aldehyde (1 mmol), malononitrile (1 mmol) or 2-aminoprop-1-ene-1,1,3-tricarbonitrile (1 mmol) and guanidine hydrochloride (10 mol%) were taken, and the mixture was stirred at 100°C in an oil bath for an appropriate amount of time as indicated in Tables 3 and 4. The progress of the reaction was monitored by thin-layerchromatography (TLC). After completion, the reaction mixture was cooled to room temperature and CH3CN (5 mL) was added, and then a precipitate was allowed to form. The precipitate was filtered, washed with CH3CN and dried. The crude product was stirred for 5 min in boiling EtOH,and the resulting precipitate was filtered. The product 4 and 9 thus obtained was found to be pure upon 1H and 13CNMR, mass spectra, elemental analyses, and TLC examination. |
80% | With nano zinc oxide In water at 80℃; for 5h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With triethylamine; In chloroform; at 60℃; for 24h; | Triethylamine (22 mmol, 2.67 g) was added to a stirred mixture of 2,3-dihydroxynaphthalene (5 mmol, 0.80 g) and picolinoyl chloride hydrochloride (12 mmol, 2.14 g) in chloroform (120 mL) at 60 °C. The reaction mixture was refluxed for 24 h. The solution was filtered, and then the filtrate was washed with 0.5 N NaOH aqueous solution several times. The chloroform layer was dried using magnesium sulfate and filtered. Evaporation of the chloroform gave a white product. The product was finally recrystallized in a solvent pair of chloroform and ether to give pure 2,3-bis(picolinoyloxy)naphthalene (L) as white solids in a 72percent yield. Anal. Calcd for C22H14N2O4: C, 71.35percent; H, 3.81percent; N, 7.56percent. Found: C, 71.30percent; H, 3.72percent; N, 7.64percent. IR (KBr, cm-1): 1762 (s, CO), 1733 (s, CO), 1306 (s), 1246 (s), 1118 (s), 891 (m), 742 (s), 696 (s). 1H NMR (CDCl3, delta): 8.68 (d, J = 4.5 Hz, 2H), 8.17 (d, J = 7.8 Hz, 2H), 7.95 (s, 2H), 7.89 (d, J = 6.3 Hz, 2H), 7.78 (t, J = 7.8 Hz, 2H), 7.54 (d, J = 6.6 Hz, 2H), 7.45 (dd, J = 7.7 Hz, 4.5 Hz, 2H). 13C NMR (CDCl3, delta): 162.95, 150.17, 147.23, 141.25, 137.04, 131.85, 127.81, 127.34, 126.66, 125.93, 121.16. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.7% | With sulfuric acid In n-heptane; dichloromethane at 20℃; for 2h; | Rearrangement of 3-tert-butoxy-2-hydroxynaphthalene (10) into 6-tert-butyl-2,3-dihydroxynaphthalene (13) To a solution of 3-tert-butoxy-2-hydroxynaphthalene (10) (150 mg, 0.69 mmol) in heptane (2 mL)/CH2Cl2 (0.5 mL), H2SO4 (trace) was added. After stirring at rt for 2 h, the white precipitate was collected by filtration. Its 1H NMR analysis revealed the presence of 6-tert-butyl-2,3-dihydroxynaphthalene (13) and 2,3- dihydroxynaphthalene in 88:12 ratio. Purification by chromatography on silica gel eluting with hexane/EtOAc 4:1 then 3:1, afforded 13 (115 mg, 76.7%) as a white powder: mp 141-143; nmax 3451, 3305, 2961, 1524, 1432, 1257, 1197, 1173 cm-1; δH 1.38 (9H, s, t-Bu), 5.44 (1H, br s, OH), 5.48 (1H, br s, OH), 7.17 (1H, s), 7.19 (1H, s), 7.37-7.44 (1H, dd, J 8.6 and 2.0 Hz), 7.54-7.56 (2H, m); δC 31.3 (CMe3), 34.6 (CMe3), 109.8, 110.4, 121.4, 123.1, 125.9, 127.6, 129.5, 143.5, 144.0, 146.9. 1H NMR profile is in agreement with the literature data corresponding to the similar structure 6-(1,1-dimethylpropyl)-2,3- dihydroxynaphthalene.11 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triethylamine / chloroform / 0 °C 2: acetic anhydride; nitric acid / 37 - 39 °C 3: sodium hydroxide; water / 100 °C | ||
Multi-step reaction with 3 steps 1: triethylamine / chloroform / 0 °C 2: nitric acid; acetic anhydride 3: sodium hydroxide / water / 100 °C | ||
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 2 h 2: nitric acid; acetic anhydride / water / 37 - 40 °C 3: water; sodium hydroxide / 1.5 h / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Stage #1: 2,3-naphthalenediol With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 0.5h; Inert atmosphere; Stage #2: 2-chloro-ethanol In N,N-dimethyl-formamide at 110℃; for 24h; Inert atmosphere; | |
90% | Stage #1: 2,3-naphthalenediol With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 0.5h; Inert atmosphere; Stage #2: 2-chloro-ethanol In N,N-dimethyl-formamide at 110℃; for 24h; | 4 The 2,3-dihydroxynaphthalene (10.000g, 62 . 5mmol) dissolved in 150mLDMF in, adding to the solution of anhydrous K 2 CO 3 (34.552g, 250 . 0mmol), in N 2 under the protection of the, heating 60C stirring 0.5h, this mixed liquid to carry out polyreaction to 2-chloro ethanol (20.000g, 250 . 0mmol), and increasing the temperature to 110 °C, at this temperature heating and stirring 24h, the reaction the resulting liquid is poured into 500 ml of water, white precipitation of the product obtained is 2,3-di2,3-bis(2-hydroxyethoxy)naphthalene. Yield 13.965g (90%) |
65% | With sodium hydroxide In ethanol Reflux; | 3.2 General procedure for the synthesis 1-a,b,c General procedure: Separately, each of the dihydroxy-substituents, catechol (a), 2,3-dihyroxynaphthalene (b), 2,2'-dihydroxy-1,1'-bisnaphthalene (c) (50 mmol), and NaOH (0.12 mol) were dissolved in 20-25 ml ethanol and 2-chloroethanol (0.12 mol) was added to this solution dropwise over 15 min. After refluxing the reaction mixture for 20 h, the resulting solid was separated by filtration. Ethanol was evaporated in vacuo and the resulting oily product was dissolved in 200 ml chloroform. The chloroform solution was washed with 3% NaOH and then with distilled water until the pH reached neutrality. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.3% | With caesium carbonate; In acetonitrile; at 160℃; under 0 - 8550.86 Torr; for 2h;Microwave irradiation; | Example 3: Methylation of other phenolic dials with dimethyl-carbonate and under m km wa ve conditions Procedure: A solution of substrate (1.074 mmo ; Table 3), Csi Oj (1 ,074 mmol), DMC (2 ml ,), mesitylene std. (100 and CHsCN (5 mL) were heated in a 30 mL air tight glass vessel, in an Anton Paar Monowave 300 microwave synthesis reactor at 160 C with a stir rate of 600 rpm. The pressure of the reaction mixture increased from 0-1 1 ,4 bar over the duration of 60/120 minutes. After 60/120 minutes, the reaction was cooled to room temperature, pressure released and the reaction mixture were analysed by GC-FID and GC- S. Results are shown in Table 3. s % yield corresponds to to-meih iated product |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With acetic anhydride; toluene-4-sulfonic acid; acetic acid; at 120℃; for 1.5h; | A mixture of 2,3-dihydroxynaphthalene (DHN) (34.4 g) and MTAG (40 g) was heated in an oil bath to 120 C on a rotary evaporator under reduced pressure until a homogeneous melt was obtained. PTSA (150 mg) in 1 : 1 v/v acetic acid/acetic anhydride (AcOH/Ac20) (1 ml_) was added and the mixture stirred at 120 C on a rotary evaporator under reduced pressure for 1 hour. TLC showed some remaining MTAG, therefore PTSA (150 mg) in 1 :1 v/v AcOH/Ac20 (1 ml_) was added and the mixture stirred at 120 C under reduced pressure for a further 30 min. TLC then showed no remaining MTAG. The dark oil was allowed to cool to room temperature overnight before being dissolved in DCM (300 mL). The solution was washed with sat. NaHC03 (4 x 50 mL), Dl water (500 mL) and brine (500 mL) before being dried (MgS04) and concentrated under reduced pressure to give a brown foaming oil (59.1 g). The foam was purified by flash chromatography using C6o silica gel (1 Kg), eluting with toluene/acetone 10:1 v/v, collecting fractions of 200 mL. Fractions 19-26 were combined and concentratedunder reduced pressure to produce a red solid (29.66 g). The red solid was triturated in IMS (150 ml_) and left at + 4C overnight to complete crystallisation. The resultant pale yellow fluffy solid was collected by filtration to give compound 5 (12.6 g, 25 %). m.p. 191 -192C, [a]D23 -26 (c 0.5 in CHCI3). 1H-NMR (DMSO- d6): delta 9.80 (1 H,), 9.67 (2H, dd, J 7.97 Hz, J 12.62 Hz), 7.45 (1 H, s), 7.28 (2H, m), 7.18 (1 H, s), 5.69 (1 H, d, J7.67 Hz), 5.48 (1 H, t, J9.65 Hz), 5.13 (2H, m, J 9.65 Hz, J7.92 Hz), 4.71 (1 H, d, J 9.90 Hz), 3.63 (3H, s), 2.01 , 2.00, 1.99 (4 x 3H, 4 x s); 13C NMR (DMSO-d6): delta 170.12, 169.92, 169.59, 167.80, 148.17, 146.35, 131.22, 128.19, 127.33, 126.16, 123.89, 1 14.05, 110.96, 98.74, 71.75, 71.63, 71.31 , 69.58, 53.15, 21.03, 20.91 , 20.81. HRMS (ESI) for C23H28O11 N [M+NH4]+: m/z calcd 494.1657; measured: 494.1646. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | In methanol; at -20℃; for 0.25h;Inert atmosphere; | Hypervavlent allylsilicon reagent 2c was prepared in a modified method for 2b. 2,3-Dihydroxynaphthalene (0.64 g, 4 mmol) and <strong>[2551-83-9]allyltrimethoxysilane</strong> (0.34 mL, 2 mmol) were dissolved in 1 mL of methanol under nitrogen atmosphere. To this mixture was added tetramethylammonium hydroxide (25 wt% in methanol; 0.84 mL, 2 mmol) dropwise at -20C. After being stirred for 15 min at the same temperature, the solvent was removed under vacuum without heating. The residue was washed once with ether containing a few drops of methanol to give a colorless powder in 99% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 2h; Green chemistry; | 2. General Procedure for the Synthesis of Aryl Tosylates (Table 2) General procedure: To a solution of hydroxyarene (25.0 mmol) in THF (15 mL) was added 10% K2CO3 (65.00 g, 47.1 mmol) or 15% NaOH (22.00 g, 82.5 mmol). After the resulting solution was cooled to 0 °C with an ice-water bath, a solution of TsCl (4.82 g, 25.3 mmol for 10% K2CO3 or 5.72 g, 30.0 mmol for 15% NaOH) in THF (35 mL) was slowly added within 15 min at 0 °C. After addition of TsCl, the ice-water bath was removed and the reaction mixture was stirred for 2 h. To the mixture was then added ethyl acetate (100 mL; more was needed when aryl tosylate has poor solubility in ethyl acetate). The two-phase mixture was separated. The organic layer was washed with water (50 mL) and dried over anhydrous MgSO4. Removal of solvent under reduced pressure gave the corresponding pure aryl tosylate. Any trace amount of TsCl, if present, can be removed by simply washing the product with hexanes. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With ammonium acetate In ethanol at 20℃; for 0.416667h; | General Procedure General procedure: In dry 100 ml Erlenmeyer flask ammonium acetate (1 mol %) in ethanol (10 ml) was taken and heated the solution. To this solution, naphthalene-2,3-diol (1.0 mmol) and aromatic benzaldehydes (4.0 mmol) were added. The reaction mixture was gently warmed on a water bath for a minute and kept aside. The completion of the reaction was monitored by TLC (hexane/ ethylacetate - 40%). The solid obtained was separated and the crude product was purified by column chromatography on silica gel using ethylacetate/hexane as the eluents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With ammonium acetate In ethanol at 20℃; for 0.5h; | General Procedure General procedure: In dry 100 ml Erlenmeyer flask ammonium acetate (1 mol %) in ethanol (10 ml) was taken and heated the solution. To this solution, naphthalene-2,3-diol (1.0 mmol) and aromatic benzaldehydes (4.0 mmol) were added. The reaction mixture was gently warmed on a water bath for a minute and kept aside. The completion of the reaction was monitored by TLC (hexane/ ethylacetate - 40%). The solid obtained was separated and the crude product was purified by column chromatography on silica gel using ethylacetate/hexane as the eluents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With ammonium acetate In ethanol at 20℃; for 0.75h; | General Procedure General procedure: In dry 100 ml Erlenmeyer flask ammonium acetate (1 mol %) in ethanol (10 ml) was taken and heated the solution. To this solution, naphthalene-2,3-diol (1.0 mmol) and aromatic benzaldehydes (4.0 mmol) were added. The reaction mixture was gently warmed on a water bath for a minute and kept aside. The completion of the reaction was monitored by TLC (hexane/ ethylacetate - 40%). The solid obtained was separated and the crude product was purified by column chromatography on silica gel using ethylacetate/hexane as the eluents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With ammonium acetate In ethanol at 20℃; for 1.08333h; | General Procedure General procedure: In dry 100 ml Erlenmeyer flask ammonium acetate (1 mol %) in ethanol (10 ml) was taken and heated the solution. To this solution, naphthalene-2,3-diol (1.0 mmol) and aromatic benzaldehydes (4.0 mmol) were added. The reaction mixture was gently warmed on a water bath for a minute and kept aside. The completion of the reaction was monitored by TLC (hexane/ ethylacetate - 40%). The solid obtained was separated and the crude product was purified by column chromatography on silica gel using ethylacetate/hexane as the eluents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With ammonium acetate In ethanol at 20℃; for 0.416667h; | General Procedure General procedure: In dry 100 ml Erlenmeyer flask ammonium acetate (1 mol %) in ethanol (10 ml) was taken and heated the solution. To this solution, naphthalene-2,3-diol (1.0 mmol) and aromatic benzaldehydes (4.0 mmol) were added. The reaction mixture was gently warmed on a water bath for a minute and kept aside. The completion of the reaction was monitored by TLC (hexane/ ethylacetate - 40%). The solid obtained was separated and the crude product was purified by column chromatography on silica gel using ethylacetate/hexane as the eluents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With ammonium acetate In ethanol at 20℃; for 0.333333h; | General Procedure General procedure: In dry 100 ml Erlenmeyer flask ammonium acetate (1 mol %) in ethanol (10 ml) was taken and heated the solution. To this solution, naphthalene-2,3-diol (1.0 mmol) and aromatic benzaldehydes (4.0 mmol) were added. The reaction mixture was gently warmed on a water bath for a minute and kept aside. The completion of the reaction was monitored by TLC (hexane/ ethylacetate - 40%). The solid obtained was separated and the crude product was purified by column chromatography on silica gel using ethylacetate/hexane as the eluents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With ammonium acetate In ethanol at 20℃; for 0.366667h; | General Procedure General procedure: In dry 100 ml Erlenmeyer flask ammonium acetate (1 mol %) in ethanol (10 ml) was taken and heated the solution. To this solution, naphthalene-2,3-diol (1.0 mmol) and aromatic benzaldehydes (4.0 mmol) were added. The reaction mixture was gently warmed on a water bath for a minute and kept aside. The completion of the reaction was monitored by TLC (hexane/ ethylacetate - 40%). The solid obtained was separated and the crude product was purified by column chromatography on silica gel using ethylacetate/hexane as the eluents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With ammonium acetate In ethanol at 20℃; for 0.416667h; | General Procedure General procedure: In dry 100 ml Erlenmeyer flask ammonium acetate (1 mol %) in ethanol (10 ml) was taken and heated the solution. To this solution, naphthalene-2,3-diol (1.0 mmol) and aromatic benzaldehydes (4.0 mmol) were added. The reaction mixture was gently warmed on a water bath for a minute and kept aside. The completion of the reaction was monitored by TLC (hexane/ ethylacetate - 40%). The solid obtained was separated and the crude product was purified by column chromatography on silica gel using ethylacetate/hexane as the eluents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With ammonium acetate In ethanol at 20℃; for 0.5h; | General Procedure General procedure: In dry 100 ml Erlenmeyer flask ammonium acetate (1 mol %) in ethanol (10 ml) was taken and heated the solution. To this solution, naphthalene-2,3-diol (1.0 mmol) and aromatic benzaldehydes (4.0 mmol) were added. The reaction mixture was gently warmed on a water bath for a minute and kept aside. The completion of the reaction was monitored by TLC (hexane/ ethylacetate - 40%). The solid obtained was separated and the crude product was purified by column chromatography on silica gel using ethylacetate/hexane as the eluents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | Intermediate (1) obtained in the above example (1) step (1) 1.3 g(5 mmol) and aluminum chloride (AlCl3) 1.3 g(10 mmol) were added in 100 ml of dichloromethane was stirred for 5 minutes at room temperature, 2,3-dihydroxy-naphthalene 4.0 g (25 mmol) was added and the mixture was stirred for 30 minutes at room temperature. Subsequently, by introducing water and the layers were separated and the organic layer was concentrated and then a mixed solvent of dichloromethane and hexane (1: 2 (v / v)) by performing column chromatography to give an orange solid of compound 1c 1.5 g (Yield: 77%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: 2,3-naphthalenediol With potassium methanolate In ethanol at 20℃; for 0.5h; Stage #2: With tetraethoxy orthosilicate In ethanol at 20℃; for 0.166667h; Stage #3: (4-hydroxy-phenyl)triphenylphosphonium bromide In ethanol for 0.5h; | 4 Preparative Example 4 Preparation of Phosphonium Compound Represented by Formula 1d Preparative Example 4 Preparation of Phosphonium Compound Represented by Formula 1d 48.1 g of 2,3-dihydroxynaphthalene was added to 50 g of ethanol (EtOH), followed by adding 21.6 g of 25% potassium methoxide solution, which in turn was completely dissolved while reacting at ambient temperature for 30 minutes. Then, 20.8 g of tetraethyl orthosilicate was added, followed by reaction at ambient temperature for 10 minutes. To the solution, a solution of 43 g of triphenyl(4-hydroxyphenyl)phosphonium bromide (previously dissolved in 50 g of EtOH) was slowly added and the mixture was allowed to further react for 30 minutes. The resulting grey solid was filtered to remove a solvent component of the solution at low pressure, thereby obtaining 77 g of a compound. The compound was identified based on NMR data as a compound represented by Formula 1d (yield: 88%). 1H NMR (300 MHz, DMSO) δ δ 7.91-7.85 (m, 3H), 7.73-7.60 (m, 12H), 7.41 (dd, J=12.1, 8.7 Hz, 6H), 7.27 (dd, J=6.0, 3.3 Hz, 2H), 7.10 (dd, J=8.7, 3.1 Hz, 6H), 6.83 (dd, J=6.0, 3.3 Hz, 2H), 6.40 (s, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | Stage #1: 2,3-naphthalenediol With sodium methylate In ethanol at 20℃; for 0.5h; Stage #2: With tetraethoxy orthosilicate In ethanol at 20℃; for 0.166667h; Stage #3: (4-hydroxy-phenyl)triphenylphosphonium bromide In ethanol for 0.5h; | 3 Preparative Example 3 Preparation of Phosphonium Compound Represented by Formula 1c Preparative Example 3 Preparation of Phosphonium Compound Represented by Formula 1c 48.1 g of 2,3-dihydroxynaphthalene was added to 50 g of ethanol (EtOH), followed by adding 21.6 g of 25% sodium methoxide solution, which in turn was completely dissolved while reacting at ambient temperature for 30 minutes. Then, 20.8 g of tetraethyl orthosilicate was added, followed by reaction at ambient temperature for 10 minutes. To the solution, a solution of 43 g of triphenyl(4-hydroxyphenyl)phosphonium bromide (previously dissolved in 50 g of EtOH) was slowly added and the mixture was allowed to further react for 30 minutes. The resulting grey solid was filtered to remove a solvent component of the solution at low pressure, thereby obtaining 80 g of a compound. The compound was identified based on NMR data as a compound represented by Formula 1c (yield: 91%). 1H NMR (300 MHz, DMSO) δ δ 7.95-7.91 (m, 3H), 7.82-7.65 (m, 12H), 7.48 (dd, J=12.3, 8.8 Hz, 6H), 7.30 (dd, J=6.0, 3.3 Hz, 2H), 7.14 (dd, J=8.8, 2.9 Hz, 6H), 6.89 (dd, J=6.0, 3.3 Hz, 2H), 6.44 (s, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | Preparative Example 1 Preparation of Phosphonium Compound Represented by Formula 1a 48.1 g of 2,3-dihydroxynaphthalene was added to 50 g of ethanol (EtOH), followed by adding 21.6 g of 25% sodium methoxide solution, which in turn was completely dissolved while reacting at ambient temperature for 30 minutes. Then, 20.8 g of tetraethyl orthosilicate was added, followed by reaction at ambient temperature for 10 minutes. To the solution, a solution of 41 g of <strong>[2751-90-8]tetraphenylphosphonium bromide</strong> (previously dissolved in 50 g of EtOH) was slowly added and the mixture was allowed to further react for 30 minutes. The resulting grey solid was filtered to remove a solvent component of the solution at low pressure, thereby obtaining 78 g of a compound. The compound was identified based on NMR data as a compound represented by Formula 1a (yield: 95%). 1H NMR (300 MHz, DMSO) delta 8.01-7.91 (m, 4H), 7.84-7.69 (m, 16H), 7.33 (dd, J=6.0, 3.3 Hz, 6H), 6.92 (dd, J=6.0, 3.3 Hz, 6H), 6.48 (s, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | Preparative Example 2 Preparation of Phosphonium Compound Represented by Formula 1b 48.1 g of 2,3-dihydroxynaphthalene was added to 50 g of ethanol (EtOH), followed by adding 28.1 g of 25% potassium methoxide solution, which in turn was completely dissolved while reacting at ambient temperature for 30 minutes. Then, 20.8 g of tetraethyl orthosilicate was added, followed by reaction at ambient temperature for 10 minutes. To the solution, a solution of 43 g of <strong>[2751-90-8]tetraphenylphosphonium bromide</strong> (previously dissolved in 50 g of EtOH) was slowly added and the mixture was allowed to further react for 30 minutes. The resulting grey solid was filtered to remove a solvent component of the solution at low pressure, thereby obtaining 79 g of a compound. The compound was identified based on NMR data as a compound represented by Formula 1b (yield: 89%). 1H NMR (300 MHz, DMSO) delta 8.04-7.96 (m, 4H), 7.82-7.73 (m, 16H), 7.39 (dd, J=6.1, 3.3 Hz, 6H), 6.99 (dd, J=6.1, 3.3 Hz, 6H), 6.53 (s, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With formic acid; In neat (no solvent); at 80℃; for 1h;Green chemistry; | General procedure: A mixture of two equivalents of aldehyde, one equivalent of 2,3-dihydroxynaphthalene (0.16 g) and two equivalents of heteroaryl amine was heated at 80oC for the appropriate amount of time as indicated in Table 1. The progress of the reaction was monitored by thin-layer chromatography(TLC). After completion, the reaction mixture was cooled to room temperature and MeOH (5 mL) was added and then a precipitate was allowed to form. The precipitate was filtered,washed with methanol and dried. The crude product was stirred for 5 min in boiling MeOH and the resulting white precipitate was filtered. The product 4 thus obtained was found to be pure upon 1H and 13C NMR, mass spectra, elemental analyses, and TLC examination. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With formic acid; In neat (no solvent); at 80℃; for 1.91667h;Green chemistry; | General procedure: A mixture of two equivalents of aldehyde, one equivalent of 2,3-dihydroxynaphthalene (0.16 g) and two equivalents of heteroaryl amine was heated at 80oC for the appropriate amount of time as indicated in Table 1. The progress of the reaction was monitored by thin-layer chromatography(TLC). After completion, the reaction mixture was cooled to room temperature and MeOH (5 mL) was added and then a precipitate was allowed to form. The precipitate was filtered,washed with methanol and dried. The crude product was stirred for 5 min in boiling MeOH and the resulting white precipitate was filtered. The product 4 thus obtained was found to be pure upon 1H and 13C NMR, mass spectra, elemental analyses, and TLC examination. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With formic acid; In neat (no solvent); at 80℃; for 0.833333h;Green chemistry; | General procedure: A mixture of two equivalents of aldehyde, one equivalent of 2,3-dihydroxynaphthalene (0.16 g) and two equivalents of heteroaryl amine was heated at 80oC for the appropriate amount of time as indicated in Table 1. The progress of the reaction was monitored by thin-layer chromatography(TLC). After completion, the reaction mixture was cooled to room temperature and MeOH (5 mL) was added and then a precipitate was allowed to form. The precipitate was filtered,washed with methanol and dried. The crude product was stirred for 5 min in boiling MeOH and the resulting white precipitate was filtered. The product 4 thus obtained was found to be pure upon 1H and 13C NMR, mass spectra, elemental analyses, and TLC examination. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With formic acid; In neat (no solvent); at 80℃; for 0.916667h;Green chemistry; | General procedure: A mixture of two equivalents of aldehyde, one equivalent of 2,3-dihydroxynaphthalene (0.16 g) and two equivalents of heteroaryl amine was heated at 80oC for the appropriate amount of time as indicated in Table 1. The progress of the reaction was monitored by thin-layer chromatography(TLC). After completion, the reaction mixture was cooled to room temperature and MeOH (5 mL) was added and then a precipitate was allowed to form. The precipitate was filtered,washed with methanol and dried. The crude product was stirred for 5 min in boiling MeOH and the resulting white precipitate was filtered. The product 4 thus obtained was found to be pure upon 1H and 13C NMR, mass spectra, elemental analyses, and TLC examination. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With formic acid; In neat (no solvent); at 80℃; for 1.5h;Green chemistry; | General procedure: A mixture of two equivalents of aldehyde, one equivalent of 2,3-dihydroxynaphthalene (0.16 g) and two equivalents of heteroaryl amine was heated at 80oC for the appropriate amount of time as indicated in Table 1. The progress of the reaction was monitored by thin-layer chromatography(TLC). After completion, the reaction mixture was cooled to room temperature and MeOH (5 mL) was added and then a precipitate was allowed to form. The precipitate was filtered,washed with methanol and dried. The crude product was stirred for 5 min in boiling MeOH and the resulting white precipitate was filtered. The product 4 thus obtained was found to be pure upon 1H and 13C NMR, mass spectra, elemental analyses, and TLC examination. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With formic acid; In neat (no solvent); at 80℃; for 1.41667h;Green chemistry; | General procedure: A mixture of two equivalents of aldehyde, one equivalent of 2,3-dihydroxynaphthalene (0.16 g) and two equivalents of heteroaryl amine was heated at 80oC for the appropriate amount of time as indicated in Table 1. The progress of the reaction was monitored by thin-layer chromatography(TLC). After completion, the reaction mixture was cooled to room temperature and MeOH (5 mL) was added and then a precipitate was allowed to form. The precipitate was filtered,washed with methanol and dried. The crude product was stirred for 5 min in boiling MeOH and the resulting white precipitate was filtered. The product 4 thus obtained was found to be pure upon 1H and 13C NMR, mass spectra, elemental analyses, and TLC examination. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With formic acid; In water; at 110℃; for 0.333333h;Green chemistry; | General procedure: Formic acid (98% aqueous solution, 0.1 mmol) was added to a mixture of heteroaryl amine (1 mmol), triethylorthoformate(1 mmol), and 2,3-dihydroxynaphthalene (1 mmol). The reaction mixture was magnetically stirred on a preheated oilbath at 110C for 20 min. The progress of the reaction was monitored by thin-layer chromatography (TLC). After completion,the reaction mixture was cooled down to room temperature, and CH3CN (5 mL) was added. The precipitate was filtered, washed with cold CH3CN, dried, and purifiedby recrystallization from ethyl acetate to give the pure products 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With formic acid In water at 110℃; for 0.333333h; Green chemistry; | General Procedure for the Synthesis of Compounds 4 General procedure: Formic acid (98% aqueous solution, 0.1 mmol) was added to a mixture of heteroaryl amine (1 mmol), triethylorthoformate(1 mmol), and 2,3-dihydroxynaphthalene (1 mmol). The reaction mixture was magnetically stirred on a preheated oilbath at 110°C for 20 min. The progress of the reaction was monitored by thin-layer chromatography (TLC). After completion,the reaction mixture was cooled down to room temperature, and CH3CN (5 mL) was added. The precipitate was filtered, washed with cold CH3CN, dried, and purifiedby recrystallization from ethyl acetate to give the pure products 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With formic acid; In water; at 110℃; for 0.333333h;Green chemistry; | General procedure: Formic acid (98percent aqueous solution, 0.1 mmol) was added to a mixture of heteroaryl amine (1 mmol), triethylorthoformate(1 mmol), and 2,3-dihydroxynaphthalene (1 mmol). The reaction mixture was magnetically stirred on a preheated oilbath at 110°C for 20 min. The progress of the reaction was monitored by thin-layer chromatography (TLC). After completion,the reaction mixture was cooled down to room temperature, and CH3CN (5 mL) was added. The precipitate was filtered, washed with cold CH3CN, dried, and purifiedby recrystallization from ethyl acetate to give the pure products 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With formic acid; In water; at 110℃; for 0.333333h;Green chemistry; | General procedure: Formic acid (98% aqueous solution, 0.1 mmol) was added to a mixture of heteroaryl amine (1 mmol), triethylorthoformate(1 mmol), and 2,3-dihydroxynaphthalene (1 mmol). The reaction mixture was magnetically stirred on a preheated oilbath at 110C for 20 min. The progress of the reaction was monitored by thin-layer chromatography (TLC). After completion,the reaction mixture was cooled down to room temperature, and CH3CN (5 mL) was added. The precipitate was filtered, washed with cold CH3CN, dried, and purifiedby recrystallization from ethyl acetate to give the pure products 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With toluene-4-sulfonic acid In neat (no solvent, solid phase) at 20℃; for 0.583333h; Green chemistry; | MOM Deprotection by pTSA General procedure: MOM ether (5 mmol) and pTSA.H2O (7.7 mmol) weretriturated well in a mortar for 5 min (in the case of entry 10trituration time was about 15 min), reaction mixture was leftat room temperature for another 30 min. After completion ofthe reaction (monitored by TLC), cold water (4oC) wasadded. The products were separated by centrifugation. Theyields of the products ranged from 85-98%. The purities andthe identities of the products were established by direct comparisonwith known compounds (TLC, Mp and IR). See supplementaryinformation for further details. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With guanidine hydrochloride In neat (no solvent) at 100℃; for 0.666667h; Green chemistry; | General procedure for the synthesis of benzo[f]chromens4a-fand 12H-benzo[5,6]chromeno[2,3-b]pyridines 9a-f General procedure: In a 25 mL round bottom flask, a mixture of 2,3-dihydroxynaphthalene (1 mmol),aldehyde (1 mmol), malononitrile (1 mmol) or 2-aminoprop-1-ene-1,1,3-tricarbonitrile (1 mmol) and guanidine hydrochloride (10 mol%) were taken, and the mixture was stirred at 100°C in an oil bath for an appropriate amount of time as indicated in Tables 3 and 4. The progress of the reaction was monitored by thin-layerchromatography (TLC). After completion, the reaction mixture was cooled to room temperature and CH3CN (5 mL) was added, and then a precipitate was allowed to form. The precipitate was filtered, washed with CH3CN and dried. The crude product was stirred for 5 min in boiling EtOH,and the resulting precipitate was filtered. The product 4 and 9 thus obtained was found to be pure upon 1H and 13CNMR, mass spectra, elemental analyses, and TLC examination. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | Stage #1: 4-amino-9-N-decyl-1,8-naphthalimide With sulfuric acid; sodium nitrite In acetic acid; propionic acid at 10℃; for 3h; Stage #2: 2,3-naphthalenediol In ethanol; acetic acid; propionic acid at 0 - 5℃; for 2h; | 6.2 2.6.1 Synthesis of (E)-2-decyl-6-((2-hydroxnaphthalen-1-yl)diazenyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione (1a) General procedure: Dry sodium nitrite (1.5mmol, 0.104g) was added to cold conc. H2SO4 (98%, 1.1mL) at such a rate that yellow fume was not evolved. The reaction temperature was gradually increased to 65°C using water bath until all the sodium nitrite was dissolved. The resulting solution was cooled to 0-5°C and then added drop wise at 5-20°C with the mixture of propionic acid and acetic acid (10mL, 1.5:8.5). The finely ground powder of 1.5mmol 4-amino-N-decyl-1, 8-naphthalimide was added portion wise at less than 10°C, and then the liquor was stirred for 3h. The obtained clear diazonium salt solution was used immediately in coupling reactions with 2-naphthol (1.5mmol) dissolved in ethanol. The previously prepared diazonium solution was added over 30-40min with vigorous stirring. The mixture was stirred further for 2hat 0-5°C and then the pH of the solution was adjusted to 4-5 using 10% sodium acetate and stirred for 1h. The resulting product was then collected by filtration, washed with warm water and then cold water till neutral and dried at 60°C for 8h in an oven. The crude product was purified by recrystallizing from DMSO several times to obtained dye 1a. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With potassium carbonate; In dichloromethane; at 20℃; for 3h;Inert atmosphere; Schlenk technique; | General procedure: In a 25ml dry Schlenk flask under argon, 1.62 mmol (0.9 equiv) of catechol (or 2 amino phenol, or 2-mercaptophenol, or salicylic alcohol), 248 mg (1. 8 mmol, 1 equiv) of potassium carbonate and 3 ml of methylene chloride were introduced. After stirring for 15 min at room temperature, 1.8 mmol (1 equiv) of fluorinated alkyne 2 was added via syringe. The mixture was stirred 3 h at room temperature. The solvent was evaporated in vacuo and the crude product was purified on silica using petroleum ether/diethyl ether as eluent (95/5) or by crystallization from diethyl ether, to give the expected products 3a-j, 7 and 9a-e with good yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With potassium carbonate In dichloromethane at 20℃; for 3h; Inert atmosphere; Schlenk technique; regioselective reaction; | 8 General procedure for the synthesis of compounds 3a-j, 7 and 9a-e General procedure: In a 25ml dry Schlenk flask under argon, 1.62 mmol (0.9 equiv) of catechol (or 2 amino phenol, or 2-mercaptophenol, or salicylic alcohol), 248 mg (1. 8 mmol, 1 equiv) of potassium carbonate and 3 ml of methylene chloride were introduced. After stirring for 15 min at room temperature, 1.8 mmol (1 equiv) of fluorinated alkyne 2 was added via syringe. The mixture was stirred 3 h at room temperature. The solvent was evaporated in vacuo and the crude product was purified on silica using petroleum ether/diethyl ether as eluent (95/5) or by crystallization from diethyl ether, to give the expected products 3a-j, 7 and 9a-e with good yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With potassium carbonate In N,N-dimethyl-formamide; toluene at 100℃; for 18h; Inert atmosphere; | 3 (Synthesis of Compound (1-5)) In an argon stream, 4.81 g (30.0 mmol) of 2,3-dihydroxynaphthalene, 4.77 g (30.0 mmol) of 3,4-difluoronitrobenzene, potassium carbonate 8. 29 g (60.0 mmol) was suspended in a mixed solution of 30 ml of dehydrated toluene and 130 ml of dehydrated N, N'-dimethylformamide and stirred at 100 ° C. for 18 hours. After cooling the reaction solution to room temperature, the reaction solution was added to 400 ml of water, and the precipitated solid was filtered and washed with methanol. The obtained solid was dried under reduced pressure to obtain a yellow powder (yield 7.12 g, yield 85%) of the objective compound (1-5). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.8% | With 2,4,6-trimethylphenylcarbene copper; dihydrogen peroxide; trimethyldodecylammonium chloride In octane at 50℃; for 7h; | 11 Example 2 In a 1000 ml three-necked flask, 512 g of n-octane was added, and then 128 g of naphthalene was added.2,4,6-trimethylphenylcarbene copper0.13g, 3.0g of tetrahexyl ammonium chloride, and the temperature is raised to 50 ° C under stirring.Then add hydrogen peroxide (concentration 30%) within 2 hours.After 500 g, the reaction was continued at 50 ° C for 5 hours to stop the reaction. The aqueous phase was extracted 3 times with 100 g of n-octane.Combine the organic phases. Taking the organic phase for liquid chromatography analysis,125.8 g (yield 78.6%) containing 2,3-dihydroxynaphthalene was shown.; The auxiliary agent is dodecyltrimethylammonium chloride, and the rest is the same as in Example 2. The yield of 2,3-dihydroxynaphthalene is83.8%. |
Multi-step reaction with 2 steps 1.1: boron tribromide / hexane / 60 h / 120 °C / Sealed tube 1.2: 0.03 h / 0 °C / Schlenk technique 2.1: 3-chloro-benzenecarboperoxoic acid / water; ethanol / 6 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.9% | Stage #1: C40H25NOS; 2,3-naphthalenediol With 3-mercaptopropionic acid In toluene at 60℃; Stage #2: With methanesulfonic acid In toluene | 1 98 g (0.1730 mol) of the obtained tertiary alcohol and 33.3 g (0.2076 mol) of dihydroxynaphthalene (manufactured by Tokyo Chemical Industry Co., Ltd.)3-Mercaptopropionic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) 2.8 g (0.02595 mol) of a toluene 600 mL solution was heated to 60 °C. To the solution, methanesulfonic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) 249.9 g (2.595 mol) was added dropwise. After the dropwise addition, the mixture was stirred for 1 hour, and then water and ethyl acetate were added thereto, and liquid separation was carried out to obtain an oil. The obtained oil was purified by column chromatography (hexane/ethyl acetate = 2/1). The target dihydroxyl group 113 g was obtained (yield: 91.9%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In neat (no solvent); at 60℃; for 0.316667h;Green chemistry; | General procedure: The mixtureof naphthalenediol (1a-b, 1 mmol), fluoro substituted benzaldehyde(2a-e, 1 mmol) and 1,3-dicarbonyl compound (3a-b,1 mmol) was stirred in a round bottom flask at 60 C under catalyst and solvent-free conditions for 20 min. After completionof the reaction (TLC) resulted solid was dissolved in THF, filtered and evaporated the solvent using rotary evaporator. After recrystallization by ethanol we obtained the pure products as white solids (4a-j). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In neat (no solvent); at 60℃; for 0.433333h;Green chemistry; | General procedure: The mixtureof naphthalenediol (1a-b, 1 mmol), fluoro substituted benzaldehyde(2a-e, 1 mmol) and 1,3-dicarbonyl compound (3a-b,1 mmol) was stirred in a round bottom flask at 60 C under catalyst and solvent-free conditions for 20 min. After completionof the reaction (TLC) resulted solid was dissolved in THF, filtered and evaporated the solvent using rotary evaporator. After recrystallization by ethanol we obtained the pure products as white solids (4a-j). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With chloranil; bis(trifluoromethanesulfonyl)amide In dichloromethane at 40℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Inert atmosphere; | |
81% | With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; | 2,2′-Biphenol-Derived Monotriflates 1; General Procedure I General procedure: According to a reported procedure,17 Tf2O (0.84 mL, 5.0 mmol) wasadded dropwise to a solution of the respective (1,1′-biphenyl)-2,2′-diol derivative (5.0 mmol, 1.0 equiv) and N-ethyldiisopropylamine(0.82 mL, 5.0 mmol) in CH2Cl2 (15 mL) at 0 °C. The reaction mixturewas slowly warmed up to rt and stirred overnight. The mixture was poured into H2O (20 mL) and then extracted with CH2Cl2 (3 × 20 mL). The combined organic layers were washed with brine (20 mL), dried (anhyd Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (PE/EtOAc as eluent) to give the desired product 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With potassium pyrosulfite; palladium 10% on activated carbon; water; ammonium formate at 100℃; Inert atmosphere; Schlenk technique; | |
72% | With tetrakis(triphenylphosphine) palladium(0); sodium formate; sodium hydrogensulfite In water at 150℃; for 15h; | 6 In the reaction vessel, mix 2,3-Naphthol (2mmol, 0.32g), ethylenediamine (3mmol, 0.18g), Pd(PPh3)4 (0.4mmol, 0.46g), sodium bisulfite (4mmol, 0.42g), sodium formate (8mmol, 0.54g), and water (10mL) were mixed uniformly, reacted at 150°C for 15 hours, cooled to room temperature after the reaction, filtered and evaporated under reduced pressure to remove unreacted substances to obtain a crude product. The product is purified by column chromatography to obtain 1,2,3,4-tetrahydrobenzo[g]quinoxaline(3f), namely compound 3f. Compound 3f is a brown oil with a yield of 72%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With potassium pyrosulfite; palladium 10% on activated carbon; water; ammonium formate at 100℃; Inert atmosphere; Schlenk technique; | |
66% | With potassium bisulfite; palladium on activated charcoal; ammonium formate In water at 120℃; for 7h; | 7 In the reaction vessel, mix 2,3-Dinaphthol (2mmol, 0.32g), 1,2-propanediamine (4mmol, 0.30g), Pd/C (0.4mol, 0.04g), potassium bisulfite ( 2mmol, 0.24g), ammonium formate (5mmol, 0.32g), and water (10mL) were mixed uniformly, and reacted at 120°C for 7 hours. After the reaction, cooled to room temperature, filtered and evaporated under reduced pressure to remove unreacted materials to obtain a crude The product, the crude product is purified by column chromatography to obtain 2-methyl-1,2,3,4-tetrahydrobenzo[g]quinoxaline (3g), namely compound 3g. Compound 3g was brown oil, and the yield was 66% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With potassium pyrosulfite; palladium 10% on activated carbon; water; ammonium formate at 100℃; Inert atmosphere; Schlenk technique; | |
65% | With sodium metabisulfite; sodium formate; palladium dichloride In water at 150℃; for 18h; | 8 In the reaction vessel, mix 2,3-Dinaphthol (5mmol, 1.3g), 1,2-diphenylethylenediamine (2mmol, 0.42g), PdCl2 (0.1mol, 0.02g), sodium metabisulfite (2mmol , 0.38g), sodium formate (6mmol, 0.41g), and water (10mL) were mixed uniformly, reacted at 150°C for 18 hours, cooled to room temperature after the reaction was completed, filtered and evaporated under reduced pressure to remove unreacted materials to obtain a crude product. The crude product is purified by column chromatography to obtain 2,3-diphenyl-1,2,3,4-tetrahydrobenzo[g]quinoxaline(3h), which is compound 3h. Compound 3h is brown oil with a yield of 65%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 81% 2: 19% | With orcinol; Acetobacterium dehalogenans veratrol-O-demethylase; Desulfitobacterium hafniense methyltransferase dhaf4611 In aq. buffer at 35℃; for 24h; Inert atmosphere; Enzymatic reaction; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56.8% | With potassium carbonate In N,N-dimethyl-formamide at 20 - 50℃; for 28h; Inert atmosphere; | 3.2.2. 1,4-Bis(hexyloxy)benzo[b]naphtho[2-e]dioxin-2,3-dicarbonitrile (3) A 2.00 g portion of compound 1 (5.03 mmol) and 0.806 g of 2,3-dihydroxynaphthalene (5.03 mmol)were dissolved under nitrogen atmosphere using 50 mL of dry DMF. A 2.09 g portion of anhydrousK2CO3 (15.10 mmol) was added and the reaction mixture was stirred vigorously at room temperaturefor 24 h, then the reaction temperature was raised to 50 °C. Reaction continued at this temperature fora further 4 h. The mixture of reaction was poured into approximately 150 mL of iced water, extractedwith chloroform, and the organic phase was dried with Na2SO4. Purification of the crude product wascarried out by crystallization with ethanol. C30H32N2O4 yield: 1.38 g (56.8%); mp: 152 °C. FT-IR (νmax,cm-1): 3080 (Ar-H), 2955-2860 (Aliph-CH), 2231 (C≡N), 1080 (C-O-C). 1H NMR (CDCl3): δ, ppm:7.70 (dd, J = 6.2, 3.3 Hz, 2H, Ar-H), 7.44 (dt, J = 6.2, 3.4 Hz, 2H, Ar-H), 7.38 (s, 2H, Ar-H), 4.28 (t, J =6.5 Hz, 4H, O-CH2), 1.88 (dt, J = 14.9, 6.7 Hz, 4H, CH2), 1.58 (quintet, J = 7.4 Hz, 4H, CH2), 1.40 (m, 8H,CH2), 0.95 (m, 6H, CH3). 13C NMR (CDCl3): δ, ppm: 146.7, 140.1, 139.0, 131.1, 127.1, 126.5, 113.3, 112.6,104.1, 76.1, 31.4, 29.9, 25.3, 22.5, 14.0.MS: (EI) m/z 484.05 [M]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In N,N-dimethyl-formamide at 50℃; |
Tags: 92-44-4 synthesis path| 92-44-4 SDS| 92-44-4 COA| 92-44-4 purity| 92-44-4 application| 92-44-4 NMR| 92-44-4 COA| 92-44-4 structure
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