Structure of 17672-21-8
*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4.5
*For Research Use Only !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 17672-21-8 |
Formula : | C8H9NO3 |
M.W : | 167.16 |
SMILES Code : | O=C(OC)C1=CC=CC(O)=C1N |
MDL No. : | MFCD01675233 |
InChI Key : | GDIJXOCHGFQHCT-UHFFFAOYSA-N |
Pubchem ID : | 205248 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 44.15 |
TPSA ? Topological Polar Surface Area: Calculated from |
72.55 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.25 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.52 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.77 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.74 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.5 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.95 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.07 |
Solubility | 1.42 mg/ml ; 0.00847 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.65 |
Solubility | 0.372 mg/ml ; 0.00223 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.53 |
Solubility | 4.91 mg/ml ; 0.0294 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.24 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
2.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.29 |
* 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 |
---|---|---|
99% | With palladium on activated charcoal; hydrogen; | Our next target was the synthesis of 2-aminophenol derivative 8, which was desirable for the construction of 4 (Scheme 5). Selective reduction of the carboxyl ester 11 by LiAlH4 in dry THF or NaBH4 in THF/MeOH gave 13 in up to 92-98% yield (Scheme 6). The deprotection of methoxyl group of 13 by AlCl3, however, gave 14 in only 61% yield, along with some unreacted 13. Although the deprotection of 13 by BBr3 also gave 14, the reaction mixture contained several unidentified by-products. Selective reduction of ester 12 by NaBH4 in THF/MeOH even did not proceed. We finally found 12 could be reduced by LiAlH4 in anhydrous THF to afford 14 in about 82% yield. Then the desirable 8 was prepared by hydrogenation catalyzed by Pd/C. |
95% | With iron; acetic acid; In ethanol; for 2h;Heating; | At room temperature, 8 g (40.58 mmol) of <strong>[89942-77-8]methyl <strong>[89942-77-8]3-hydroxy-2-nitrobenzoate</strong></strong> were dissolved in 160 ml of a mixture (1:1) of acetic acid and ethanol. 9.971 g (178.55 mmol) of iron powder were added to the solution, and the mixture was heated at the boil for 2 h. The mixture was cooled to room temperature, 50 ml of water were added and the mixture was extracted twice with 100 ml of ethyl acetate. The organic phase was washed with dilute sodium bicarbonate solution until neutral and dried over sodium sulfate. The solvent was removed under reduced pressure, giving 6.50 g (95% of theory) of the desired methyl 2-amino-3-hydroxybenzoate. 1H-NMR (400 MHz, DMSO-d6 delta in ppm) 9.66 (s, 1H), 7.20 (d, 1H), 6.81 (d, 1H), 6.39 (t, 1H), 6.09 (br. s, 2H), 3.78 (s, 3H). 700 mg (4.19 mmol) of methyl 2-amino-3-hydroxybenzoate, 877 mg (4.19 mmol) of 2,4-dichlorobenzoyl chloride and 210 mg (0.838 mmol) of 4-methylbenzenesulfonic acid monohydrate were suspended 10 ml of xylene in a microwave vial. The vial was sealed with a septum cap and the mixture was heated in a Biotage Initiator Sixty microwave at 160 C. for 25 min. After cooling to room temperature, the solvent was removed under reduced pressure and the crude product was purified by column chromatography (n-heptane:ethyl acetate 4:1?ethyl acetate), giving 500 mg (35% of theory) of methyl 2-(2,4-dichlorophenyl)-1,3-benzoxazole-4-carboxylate. 1H-NMR (CDCl3 delta in ppm): 8.21 (d, 1H), 8.08 (d, 1H), 7.81 (dd, 1H), 7.59 (d, 1H), 7.48 (t, 1H), 7.42 (dd, 1H), 4.05 (s, 3H). 450 mg (1.40 mmol) of methyl 2-(2,4-dichlorophenyl)-1,3-benzoxazole-4-carboxylate and 0.838 ml of 2 N aqueous sodium hydroxide solution were dissolved in 10 ml of THF and 2 ml of water. The solution was stirred at room temperature overnight, resulting in the precipitation of a solid. The suspension was acidified with 2 N hydrochloric acid and the resulting solid was filtered off with suction. The solid was air-dried, giving 300 mg (66% of theory) of the desired 2-(2,4-dichlorophenyl)-1,3-benzoxazole-4-carboxylic acid. 1H-NMR (CDCl3 delta in ppm): 11.62 (br. s, 1H), 8.23-8.18 (m, 2H), 7.88 (d, 1H), 7.67 (d, 1H), 7.60 (t, 1H), 7.49 (dd, 1H). 250 mg (0.81 mmol) of 2-(2,4-dichlorophenyl)-1,3-benzoxazole-4-carboxylic acid, 132 mg (0.97 mmol) of 1-hydroxy-1H-benzotriazole, 171 mg (0.89 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 10 mg of DMAP were dissolved in 5 ml of dichloromethane. The mixture was stirred at room temperature for 15 min, and 1.78 ml of a 0.5 M solution of ammonia in 1,4-dioxane were then added dropwise. The mixture was stirred at room temperature for 2 h and the organic phase was washed twice with 0.5 N hydrochloric acid and once with dilute sodium bicarbonate solution. The solvent was removed under reduced pressure and the residue was suspended in acetonitrile and then heated in an ultrasonic bath. The solid was filtered off with suction and air-dried. This gives 120 mg (45% of theory) of 2-(2,4-dichlorophenyl)-1,3-benzoxazole-4-carboxamide. 1H-NMR (DMSO-d6 delta in ppm): 8.42 (br. s, 1H), 8.33 (d, 1H), 8.07-8.01 (m, 3H), 7.98 (d, 1H), 7.71 (d, 1H), 7.62 (dd, 1H). |
palladium/carbon catalyst; In methanol; | 2nd Stage Preparation of Methyl (2-Amino-3-hydroxy)benzoate Under a nitrogen atmosphere a palladium/carbon catalyst was suspended in anhydrous methanol (150 ml). To this suspension was added methyl (3-hydroxy-2-nitro) benzoate from Stage 1 (4 g; 20.3 mM). The mixture was left under a hydrogen atmosphere for 41/2 hours. The catalyst was removed by filtration through a "celite" pad, and the solvent removed from the filtrate to yield an orange/brown product. |
With hydrogen;palladium on activated charcoal; In ethyl acetate; at 25℃; under 760.051 Torr; for 4h; | Example 113 Cmethyl 2-amino-3-hydroxybenzoate; A suspension of <strong>[89942-77-8]methyl <strong>[89942-77-8]3-hydroxy-2-nitrobenzoate</strong></strong> (14 g, 71 mmol) and 10% Pd/C (1.4 g) in ethyl acetate (300 mL) was purged in 1 atm hydrogen and stirred at 25 C. for 4 hr. The mixture was filtered, and the filtrate was concentrated to give methyl 2-amino-3-hydroxybenzoate (11.5 g, yield 97%) as a light yellow solid. 1H-NMR (400 MHz, CDCl3-d) delta 3.88 (s, 1H), 5.84 (s, br 3H), 6.50-6.54 (t, J=8.0 Hz, 1H), 6.84-6.86 (d, J=7.2 Hz, 1H), 7.47-7.49 (d, J=7.6 Hz, 1H); LC-MS (ESI) m/z 168 [M+1]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In methanol; water; | Step 1 Methyl-2-amino-3-hydroxybenzoate To a solution of 2 g (13.1 mmol) of 2-amino-3-hydroxybenzoic acid in 60 mL of CH3OH at 0 C. was bubbled HCl gas until the solution was saturated. The reaction was heated at reflux for 12 h. The reaction mixture was concentrated and dissolved in 30 mL of water. The solution was neutralized with sat'd NaHCO3 solution and extracted with EtOAc. The organic fractions were dried over MgSO4, filtered and the filtrate was concentrated to give 1.8 g of the title compound as a brown solid. | |
0.90 g (83%) | In methanol; | EXAMPLE 30 2-Amino-3-hydroxy-benzoic acid methyl ester To a solution of 1.0 g (6.53 mmol) of 3-hydroxyanthranilic acid in 15 mL of methanol was added 5.0 mL of BF3 -methanol complex and the resulting solution was heated to reflux for 24 h. After cooling to room temperatue the reaction mixture was poured into saturated sodium carbonate solution and then extracted with ether. The combined organics were washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo to provide 0.90 g (83%) of the desired product as a brown solid. Electrospray Mass Spec: 167.8 (M+H)+ |
0.90g (83%) | In methanol; | Example 30 2-Amino-3-hydroxy-benzoic acid methyl ester To a solution of 1.0g (6.53mmol) of 3-hydroxyanthranilic acid in 15mL of methanol was added 5.0mL of BF3-methanol complex and the resulting solution was heated to reflux for 24h. After cooling to room temperature the reaction mixture was poured into saturated sodium carbonate solution and then extracted with ether. The combined organics were washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo to provide 0.90g (83%) of the desired product as a brown solid. Electrospray Mass Spec: 167.8 (M+H)+ |
With thionyl chloride; In methanol; for 2h;Reflux; | To a solution of 2-amino-3-hydroxybenzoic acid (10 g, 65 mmol) in anhydrous methanol (300 mL) was added thionyl chloride (16 g, 0.13 mol) dropwise at room temperature. The solution was heated to reflux for 2 hours. On completion, the resulting solution was concentrated in vacuo to give compound B-257 (10 g, crude) as a red solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; at 0℃;Reflux; | To a stirred solution of 2-amino-3-hydroxybenzoic acid (1.22 g, 8.0 mmol) in MeOH (80 mL) was added SOCI2 (9.52g, 80.0 mmol) dropwise at 0C. The mixture was then heated at reflux overnight. Most of the methanol was removed and the residue was partitioned between DCM and saturated aqueous NaHC03. The organic phase was washed with brine, dried over sodium sulfate and the solvent was removed under reduced pressure to give methyl 2-amino- 3-hydroxybenzoate (1.27 g, 95%). LC-MS (ES-API); rt 8.09 min; m/z calculated for C8H9N03 [M+H]+ 168.1, found 168.1. | |
With hydrogenchloride; toluene-4-sulfonic acid; for 12h;Reflux; | To a solution of 3-hydroxyanthranilic acid (1.93 g, 12.6 mmol) in saturated HCl MeOH (40 mL) was added p-toluenesulfonic acid (p-TsOH) monohydrate (95 mg, 0.5 mmol). The reaction mixture was stirred at reflux temperature for 12 h. The solvent was evaporated under reduced pressure. The residue was dissolved in AcOEt. The organic layer was washed with saturated KHCO3 solution, water and brine, and dried over MgSO4. After filtration, the solvent was evaporated under reduced pressure. The residue was dissolved in Et2O. The insoluble material was filtered off. The filtrate was concentrated in vacuo. To a solution of methyl 3-hydroxyanthranilate (1.22 g, 7.37 mmol) in CH2Cl2 (10 mL) was added Et3N (1.85 g, 18.25 mmol), followed by dropwise addition of a solution of thiophosgene (923 mg, 8.03 mmol) in CH2Cl2 (2 mL) with stirring at ambient temperature for 5 min. The reaction mixture was concentrated in vacuo. The residue was dissolved in AcOEt. The organic layer was washed with 1-N HCl, water and brine and dried over MgSO4. After filtration, the solvent was evaporated under reduced pressure to give a solid, which was crystallized from AcOEt/n-hexane to afford methyl 2-mercaptobenzo[d]oxazole-4-carboxylate (7a) (1.28 g, 84%). 2-bromo-N-(2,6-diisopropylphenyl)hexanamide (2e) was obtained from1 using 6-bromohexanoic acid in place of bromoacetic acid in a manner similar to that described for compound 3a. To a stirred solution of the thus obtained thiol (1.05 g, 5.0 mmol) and 2e (1.77 g, 5.0 mmol) in DMF (20 mL) were added K2CO3 (1.04 g, 7.5 mmol) and 18-crown-6 (132 mg, 0.5 mmol). The reaction mixture was stirred at 80 C for 2 h and diluted with water. The organic layer was extracted with Et2O, washed with water and brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography and eluted with acetone/n-hexane (1:5) to give a solid, which was recrystallized from acetone/n-hexane to afford 12a (1.84 g, 76%) as colorless needles. | |
0.52 g | With thionyl chloride; for 16h;Reflux; | 3-Hydroxyanthranilic acid (0.47 g) was mixed with methanol (5.1 mL) and SOCl2 (0.11 mL) and reacted under reflux for 16 hours to obtain 3-hydroxyanthranilic acid methyl ester (3- hydroxyanthranilic acid methyl ester (yield: 0.52 g), which was dissolved in 3N NaOH (15 mL) with di-tert-butyl dicarbonate (0.89 mL)To obtain methyl 2- (tert-butoxycarbonylamino) -3-hydroxybenzoate [2- (tert-butoxycarbonylamino) -3-hydroxybenzoate, 0.58 g, compound 2].The anhydrous acetone solution (5.4 mL) of Compound 2 (0.29 g) was reacted with K2CO3 (0.5 g) and N- (3-bromopropyl) phthalimide, Synthesis of 2- (tert-butoxycarbonylamino) -3- [3- (1,3-dioxoisoindolin-2-yl) propoxy] benzoate - (1,3-dioxoisoindolin-2-yl) propoxy] bozoate, 0.32 g, compound 3} and compound 3 reacted with c-HCl (1.2 mL) with stirring at 100 for 48 hours and then concentrated under reduced pressure . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; In dichloromethane; at 20℃; | To a solution of compound 2.6 (3.45 g, 10 mmol) in 60 ml of dry CH2Cl2 was added 10 ml of freshly distilled oxalyl chloride. The reaction mixture was stirred for 10 minutes and 0.3 ml of dimethyl formamide was added to initiate the reaction. The reaction mixture was stirred for 2 hours at room temperature and the solvent was removed by evaporation. The resultant yellow solid was dried under vacuum for 3 hours. The yellow solid was then dissolved in 20 ml of dry CH2Cl2 and transferred via cannula to a solution of <strong>[17672-21-8]methyl 2-amino-3-hydroxybenzoate</strong> (1.67 g, 10 mmol) dissolved in 40 ml of dry CH2Cl2 and 3 ml of pyridine. The reaction mixture was stirred at room temperature overnight and then diluted with dichloromethane. The solution was washed with 1% HCl, satd. aq. NaHCO3 and satd. aq. NaCl. The organic layer was dried over anhydrous Na2SO4 and the solvent was evaporated to give a residue which was subjected to column chromatography using CH2Cl2 as eluent to afford a light yellow solid (3.8 g, 77%): mp 157-158 C.; Rf 0.329 (CH2Cl2); 1H NMR delta 3.79 (s, 3H), 5.29 (s, 2H), 7.13-7.39 (m, 8H), 7.50-7.55 (m, 4H), 7.65 (dd, 1H, J=7.5, 1.5 Hz), 7.80 (brd, 1H, J=8.1 Hz), 8.31 (brd, 1H, J=7.8 Hz), 8.50 (dd, 1H, J=7.5, 1.8 Hz); 13C NMR delta 52.23, 70.71, 113.76, 114.71, 115.76, 121.18, 122.51, 122.98, 123.62, 124.73, 125.62, 126.35, 126.50, 126.69, 127.68, 127.87, 132.31, 133.66, 136.28, 139.91, 150.87, 151.20, 157.89, 163.46, 164.40, 167.11; CIMS m/z 495 (MH+); HRMS m/z calc'd for C29H23N2O6: 495.1556, found 495.1553. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With palladium on activated charcoal; hydrogen; In ethanol; at 0 - 20℃; for 4h;Inert atmosphere; | General procedure: 2-nitrobenzene-1,3-diol (1.00 g, 6.5 mmol)Of ethanol (20 ml)Palladium on carbon in the solution (200 mg)It was added at 0 under an argon atmosphere.After hydrogen substitution, and stirred at room temperature for 4 hours.After completion of the reaction, it was filtered through Celite, and the filtrate was concentrated under reduced pressure, to give the title compound (827 mg, 100%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.86 g (57%) | In pyridine; | EXAMPLE 31 3-Hydroxy-2-(4-methoxy-benzenesulfonylamino)-benzoic acid methyl ester To a solution of 0.748 g (4.48 mmol) of the product of Example 30 in 10.0 mL of pyridine was added 0.928 g (4.48 mmol) of p-methoxybenzenesulfonyl chloride. The reaction mixture was stirred for 24 h at room temperature and then diluted with chloroform and washed with 5% HCl solution and water. The organic layer was then dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated with ether-hexanes and the resulting solid was filtered and dried to provide 0.86 g (57%) of the desired product as a tan solid. Electrospray Mass Spec: 338.2 (M+H)+ |
0.86g (57%) | In pyridine; | Example 31 3-Hydroxy-2-(4-methoxy-benzenesulfonylamino)-benzoic acid methyl ester To a solution of 0.748g (4.48mmol) of the product of Example 30 in 10.0mL of pyridine was added 0.928g (4.48mmol) of p-methoxybenzenesulfonyl chloride. The reaction mixture was stirred for 24h at room temperature and then diluted with chloroform and washed with 5% HCl solution and water. The organic layer was then dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated with ether-hexanes and the resulting solid was filtered and dried to provide 0.86g (57%) of the desired product as a tan solid. Electrospray Mass Spec: 338.2 (M+H)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | Carbonyldiimidazole (CDI) (5.10 g, 31.5 mmol) was dissolved in 50 ml dry THF with stirring at room temperature under an argon atmosphere, and 2-(benzyloxy)benzoic acid (compound 2.4) (7.18 g, 31.5 mmol) was added to the mixture. After the evolution of CO2 ceased (ca. 5 min) the reaction mixture was stirred for an additional 10 minutes and <strong>[17672-21-8]methyl 2-amino-3-hydroxybenzoate</strong> (3.5 g, 21 mmol) was added. After stirring for an additional 10 minutes at room temperature, the reaction mixture was heated under reflux for 18 hours. The reaction mixture, brown in color, was concentrated and dissolved in a minimum volume of ethyl acetate (EtOAc). Silica gel (60-100 mesh) was added to make a slurry and solvent was evaporated to dryness. Column chromatography was performed using 20% EtOAc in hexane to give a light yellow solid (6.9 g, 87%): mp 104-105 C.; Rf 0.328 (20% EtOAc in hexanes); 1H NMR delta 3.80 (s, 3H), 5.50 (s, 2H), 7.05 (d, 1H, J=8.1 Hz), 7.10 (t, 1H), 7.24 (m, 2H), 7.34 (m, 3H), 7.47 (m, 3H), 7.61 (d, 1H, J=7.8 Hz), 8.27 (d, 1H, J=9.0 Hz), 9.28 (brs, 1H, NH), 12.27 (s, 1H, OH); 13C NMR delta 52.20, 70.80, 113.34, 120.94, 121.27, 121.58, 122.97, 125.70, 126.05, 126.93, 128.01, 128.21, 128.60, 132.69, 133.93, 136.22, 150.76, 157.01, 165.51, 167.57; CIMS m/z 378 (MH+); HRMS m/z calc'd for C22H20NO5: 378.1341, found 378.1343. |
A148171 [401568-70-5]
Methyl 2-amino-4-hydroxybenzoate
Similarity: 0.93
A485990 [5701-87-1]
2-Amino-3,4-dimethoxybenzoic acid
Similarity: 0.89
A148171 [401568-70-5]
Methyl 2-amino-4-hydroxybenzoate
Similarity: 0.93
A234188 [67973-80-2]
Methyl 3-amino-5-hydroxybenzoate
Similarity: 0.88
A163907 [41684-07-5]
4-Amino-3-(methoxycarbonyl)benzoic acid
Similarity: 0.87
A148171 [401568-70-5]
Methyl 2-amino-4-hydroxybenzoate
Similarity: 0.93
A485990 [5701-87-1]
2-Amino-3,4-dimethoxybenzoic acid
Similarity: 0.89