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Chemical Structure| 3114-61-2 Chemical Structure| 3114-61-2
Chemical Structure| 3114-61-2

3-Methoxy-2-nitrophenol

CAS No.: 3114-61-2

4.5 *For Research Use Only !

Cat. No.: A574522 Purity: 96%

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Product Details of [ 3114-61-2 ]

CAS No. :3114-61-2
Formula : C7H7NO4
M.W : 169.13
SMILES Code : OC1=CC=CC(OC)=C1[N+]([O-])=O
MDL No. :MFCD16876801
InChI Key :URFJTCWCTWGRBB-UHFFFAOYSA-N
Pubchem ID :15654643

Safety of [ 3114-61-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 3114-61-2 ]

* 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.

  • Downstream synthetic route of [ 3114-61-2 ]

[ 3114-61-2 ] Synthesis Path-Downstream   1~29

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  • [ 91-66-7 ]
  • 4-methoxy-2-methylbenzo[d]oxazole [ No CAS ]
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  • [ 149353-19-5 ]
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  • N-[6-Methoxy-2-{3-(5-methyl-4-phenyl-1H-imidazol-1-yl) propoxy}]phenyl-N'-pentylurea [ No CAS ]
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  • [ 601-89-8 ]
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  • [ 108-46-3 ]
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  • [ 601-89-8 ]
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YieldReaction ConditionsOperation in experiment
37% With sodium hydroxide; In water; at 40℃; for 0.25h; Dimethylsulfate (2.7 mL, 0.058 mmol) was added carefully to 2-nitrobenzene-1,3-diol (2.5 g, 0.232 mmol) and the mixture was stirred vigorously while 10% NaOH solution (21 mL) was added and the temperature was kept below 40 C. After about 15 min, the mixture was cooled and then filtered. The filtrate was collected and acidified with 10% HCl, and extracted with ether (3×25 mL). The organic layer was dried (MgSO4), filtered, and concentrated under vacuum. Chromatography (10-30% EtOAc/hexanes) provided 9A10 (1 g, 37%).
  • 12
  • [ 3114-61-2 ]
  • 6-iodo-3-methoxy-2-nitro-phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With iodine; sodium hydrogencarbonate; at 0 - 20℃; for 1.0h; Step 2: 6-Iodo-<strong>[3114-61-2]3-methoxy-2-nitrophenol</strong> A mixture of 1.36 g (8 mmol) of the product of Step 1 and 0.68 g (8 mmol) of sodium bicarbonate was sonicated at room temperature until it become homogenous. The resulting mixture was cooled to O0C and 2.04 g (8 mmol) of iodine was added. After stirring for 1 h at room temperature the precipitate formed was filtered off, dried and recrystallized from ethyl ether to give 2.28 g (96% yield of pure title compound as an orange crystals; 1H NMR (CDCl3) 3.92 (s, 3H, OMe); 6.41 (d, IH, CH J = 9Hz); 7.82 (d, IH5 J=9Hz); 10.37 (s, IH5 OH).
  • 13
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YieldReaction ConditionsOperation in experiment
With ammonia; water; In acetonitrile; at 20℃; for 0.5h; Example 1Preparation of (6-Methoxy-7-nitrobenzofuran-3-yl)(3,4,5-trimethoxyphenyl)methanone:Step 1: 2-Nitro-3-methoxy phenol To a mixture of 2.01 g (1.3 mmol) of 2-nitroresorcinol in 15 ml of dry pyridine 0.28 ml (1.36 mmol) of acetic anhydride was added dropwise at O0C. The resulting mixture was allowed to warm to room temperature. After 1 h of stirring at room temperature the solvent was removed by evaporation in vacuo and the residue diluted to 10 ml with anhydrous acetonitrile. To this 2 g of anhydrous potassium carbonate was added followed by the addition of 1.5 ml of methyl iodide. The resulting suspension was stirred overnight at room temperature, filtered off and filtrate evaporated to dryness under reduced pressure to give 2.63 g of crude 3-methoxy-2-nitrophenyl acetate. This was dissolved in 15 ml of acetonitrile and 2 ml of concentrated ammonium hydroxide was added. The resulting mixture was allowed to stand for 30 minutes at room temperature and evaporated to diyness under reduced pressure. The residue was purified by flash column chromatography to give 1.36 g (62% yield) of pure title compound as red crystals; 1H <n="65"/>NMR (CDCl3) 3.92 (s, 3H, OMe); 6.51 (d, IH5 CH5 J = 8.5 Hz); 6.68 (d, IH, CH5 J= 8.5 Hz); 7.35 (m, IH, CH); 10.18 (s, IH5 OH).
  • 14
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  • [ 601-89-8 ]
  • [ 74-88-4 ]
  • [ 3114-61-2 ]
YieldReaction ConditionsOperation in experiment
32% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 7.0h; To a stirred solution of 28 (25.0 g, 161 mmol) in DMF (500 mL) were added K2CO3 (6.80 g, 49.2 mmol) and MeI (11.0 mL, 177 mmol). After stirring for 7 h at room temperature, the reaction mixture was concentrated in vacuo and diluted with water. The resulting mixture was washed with EtOAc; the aqueous layer was acidified with 1 mol/L HCl and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (n-hexane-EtOAc = 2:1) to give 29 (8.78 g, 51.9 mmol, 32%) as a yellow oil. 1H NMR (CDCl3, 400 MHz): δ 3.95 (3H, s), 6.54 (1H, dd, J = 8.6, 1.2 Hz), 6.71 (1H, dd, J = 8.6, 1.2 Hz), 7.40 (1H, t, J = 8.6 Hz), 10.22 (1H, s).
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 7.0h; 3-Methoxy-2-nitrophenol To a solution of 2-nitroresoreinol (25.0 g) in DMF (500 mL) were added potassium carbonate (6.8 g) and methyl iodide (11.0 mL), followed by stirring at room temperature for 7 hours. The solvent was evaporated under reduced pressure, and then to the residue was added water, followed by washing with ethyl acetate. The aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate. The extracted layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain the desired product (8.78 g) as a yellow oil. 1H NMR (CDCl3, 400 MHz): δ 3.95 (3H, s), 6.54 (1H, dd, J=8.6, 1.2 Hz), 6.71 (1H, dd, J=8.6, 1.2 Hz), 7.40 (1H, t, J=8.6 Hz), 10.22 (1H, s).
1.6 g With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20℃; for 0.5h; 5 g of 2-nitrobenzene-1,3-diol was dissolved in N,N-dimethylformamide (75 mL), and then potassium carbonate (1.3 g, 0.3 equivalent) and methyl iodide (2.23 mL, 1.1 equivalents) were added thereto at 0 C., followed by stirring at room temperature for 30 minutes. The formation of the product was confirmed by TLC, and then distilled water was added to stop the reaction, followed by extraction using ethyl acetate. The organic phase was washed by 2 M hydrochloric acid (20 mL) and then dried over anhydrous magnesium sulfate, followed by filtration, and thus obtaining 1.6 g of the title compound by purification of the residue obtained by vacuum concentration of the filtrate through silica gel column chromatography (hexane:ethyl acetate=85:15).MS (ESI) m/z: 168 (M-H)-
1.6 g In N,N-dimethyl-formamide; at 0 - 20℃; for 0.5h; 5 g of 2-nitrobenzene-1,3-diol was dissolved in N,N-dimethylformamide (75 mL), and then potassium carbonate(1.3 g, 0.3 equivalent) and methyl iodide (2.23 mL, 1.1 equivalents) were added thereto at 0C, followed by stirring atroom temperature for 30 minutes. The formation of the product was confirmed by TLC, and then distilled water wasadded to stop the reaction, followed by extraction using ethyl acetate. The organic phase was washed by 2 M hydrochloricacid (20 mL) and then dried over anhydrous magnesium sulfate, followed by filtration, and thus obtaining 1.6 g of thetitle compound by purification of the residue obtained by vacuum concentration of the filtrate through silica gel columnchromatography (hexane:ethyl acetate = 85:15).MS (ESI) m/z: 168 (M-H)-

  • 19
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  • [ 40925-69-7 ]
YieldReaction ConditionsOperation in experiment
98% With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃; under 760.051 Torr; for 2.5h; To a stirred solution of 29 (8.78 g, 51.9 mmol) in EtOH (250 mL) was added 10% Pd-C (1 g) and the reaction mixture was stirred for 2.5 h at room temperature under a hydrogen atmosphere (1 atm). The reaction mixture was filtered through a pad of Celite. The filtrate was concentrated in vacuo to give 30 (7.09 g, 51.0 mmol, 98%) as a yellow solid. 1H NMR (CDCl3, 400 MHz): δ 3.85 (3H, s), 6.46 (1H, d, J = 7.9 Hz), 6.48 (1H, d, J = 7.9 Hz), 7.40 (1H, t, J = 7.9 Hz), 10.22 (1H, s).
With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; for 2.5h; 2-Amino-3-methoxyphenol To 10%-palladium carbon (1.00 g) were added ethanol (250 mL) and the compound of Example 106 (8.78 g), followed by stirring at room temperature for 2.5 hours under hydrogen atmosphere. The insoluble materials were removed by filtration through Celite and the solvent of the filtrate was evaporated under reduced pressure to obtain the desired product (7.09 g) as a yellow powder. EIMS (+): 139 [M]+ 1H NMR (CDCl3, 400 MHz): δ 3.85 (3H, s), 6.46 (1H, d, J=7.9 Hz), 6.48 (1H, d, J=7.9 Hz), 7.40 (1H, t, J=8.6 Hz), 10.22 (1H, s).
  • 20
  • [ 3114-61-2 ]
  • C23H28F3NO7 [ No CAS ]
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  • C15H12F3NO7 [ No CAS ]
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  • [ 3114-61-2 ]
  • C14H12F3NO5 [ No CAS ]
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  • [ 3114-61-2 ]
  • [ 1013036-99-1 ]
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  • [ 1013037-03-0 ]
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  • [ 1013037-07-4 ]
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  • [ 1013036-93-5 ]
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  • [ 3114-61-2 ]
  • 2,2,2-trifluoro-N-(2-hydroxy-6-methoxyphenyl)acetamide [ No CAS ]
  • 28
  • [ 150-19-6 ]
  • [ 3114-61-2 ]
  • [ 16292-95-8 ]
  • [ 704-14-3 ]
YieldReaction ConditionsOperation in experiment
4.7%; 34%; 29% With bismuth (III) nitrate pentahydrate; In acetone; at 0℃; for 20.0h; General procedure: To a solid mixture of phenol (1-3 equiv) and Bi(NO3)35H2O (1 equiv) or Fe(NO3)39H2O (1 equiv) was added acetone (10 ml/mmol). The resulting mixture was stirred at room temperature under air or at reflux for 2-24 hours, Tables 1 and 2. When the reaction was completed the insoluble materials were filtered off using a pad of Celite and the residue was washed by acetone (ca. 5 ml/mmol). The filtrate was treated by NaHCO3 (0.1 g/mmol) until evolution of CO2 stopped. Insoluble material was filtered off again, and the solvent was removed under vacuum in a water bath 25-35C. The nitrated products were separated or purified using silica gel chromatography, to give pure phenolic compounds. All products were characterized by 1H NMR,13C NMR and IR and were identified by comparison of the spectral data and melting points with those reported in literature and characterized.
  • 29
  • [ 3114-61-2 ]
  • 2-(2-(diethylamino)ethoxy)-6-methoxyaniline [ No CAS ]
 

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