Benzoic acid, 4-amino-3,5-dimethyl-, methyl ester

Scheme 5, step B. To a solution ofmethyl3, 5-dimethyl-4-nitrobenzoate (10.0 g, 0.0478 mol) in methanol (100 mL), iron powder (15.7 g, 0.2869 mol) and 37percent HCl (1.72g, 0.0478 mol) is added at 0 °C. The reaction is heated at 80 oc for 16 hours. The mixture is cooled to room temperature and filtered through Celite™ bed and washed withmethanol followed by evaporation of filtrate to dryness to afford the title compound as abrown solid (7.8 g, 99percent). Mass spectrum (m/z): 180.2 (M+ 1).To a solution of methyl 3, 5-dimethyl-4-nitrobenzoate (10.0 g, 0.0478 mol) in MeOH (100 mL), iron powder (15.7 g, 0.2869 mol) and 37percent HC1 (1.72 g, 0.0478 mol) are added at 0 °C. The reaction mixture is heated at 80 °C for 16 hours. The mixture is cooled to room temperature, filtered through diatomaceous earth, and washed with MeOH. The filtrate is concentrated to afford the title compound as brown solid (7.8 g, 99percent). Mass spectrum (m/z): 180.2 (M+H)General procedure: The compound obtained from Preparation Example 86-2 was dissolved in methanol (100ml), and the solution was allowed to react using palladium (1.25g) and hydrogen and filtered using Celite pad. Filtrate was separated by column chromatography to obtain the title compound (9.75g, 93percent). [1164] NMR:1H-NMR(500HMz, CDCl3); delta 7.34 (d, 1H), 7.25 (s, 1H), 7.12 (d, 1H), 3.87 (s, 3H), 3.71 (brs, 2H), 2.56 (q, 2H), 1.27 (t, 3H)4) dropping a 12percent by mass aqueous solution of sodium hydroxide into the mixture III, The control temperature is not higher than 60 ° C, and after the end of the dropwise addition, the reaction temperature is controlled at 130 ° C.The reaction pressure is 6 atmospheres, the reaction is 3.5 hours, and the mixture is cooled to room temperature to obtain a mixture IV;The molar ratio of methyl 4-amino-3-methylbenzoate to sodium hydroxide in aqueous sodium hydroxide solution was 1:1.75.5) Pour the mixture IV into 3.5 volumes of water and add dichloromethane to extract.The ratio of methyl 4-amino-3-methylbenzoate to dichloromethane is 1 g: 5 mL;After the organic layer is washed with water and dried over anhydrous sodium sulfate, The solvent was concentrated by evaporation on a rotary evaporator to give the product.The molar yield was 99.1percent and the GC purity was 98.9percent.

Molecular Weight:179.22
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:179.094628657
Monoisotopic Mass:179.094628657
Topological Polar Surface Area:52.3
Heavy Atom Count:13
Complexity:181
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes