Benzoic acid, 2-amino-6-methyl-, methyl ester

A mixture of methyl 2-methyl-6-nitrobenzoate (3.80g, 19.5 mmol) and 10percent palladium-carbon (containing 50percent water) (1.03g) was stirred under a hydrogen atmosphere in methanol (20mL) at 20-25°C for 1.5 hours. Example 130 Synthesis of (+/-)-Isopropyl 5- [acetyl- (3, 5-bistrifluoromethylbenzyl) amino] -6-methyl- tetrahydrobenzo [b] azepine-1-carboxylate Step 1. Preparation of 2-Amino-6-methyl-benzoic acid methyl ester. Dissolve 2-Amino-6-methyl-benzoic acid (3.00 g, 19.8 mmol) in ethylacetate (100 mL) and ethanol (100 mL) and add (trimethylsilyl) diazomethane (19.8 mL, 39.7 mmol, 2M in hexane) at room temperature and stir the solution for 1 h 30 min. Remove the solvent under reduced pressure to afford the title compound (3.30 g, quantitative). lH NMR (CDC13, 300 MHz) S 2.43 (s, 3H), 3.89 (s, 3H), 5.11 (brs, 2H), 6.52 (m, 2H), 7.08 (t, J = 7.7 Hz, 1H). MS (ES+): 166 (M+H).2.0 M diethyl ether solution of trimethylsilyldiazomethane was added under ice cooling to a mixture of 15.1 g of 2-amino-6-methylbenzoic acid, 150 mL of ethyl acetate, 150 mL of ethanol. After the mixture was stirred at ambient temperature for 4 hr, the reaction mixture was concentrated under reduced pressure to obtain 16.5 g of methyl 2-amino-6-methyl benzoate. Methyl 2-amino-6-methylbenzoate The methyl 6 -methylanthranilate so prepared (4.23 g, 0.026 mol) was dissolved in 25 ml of acetic acid and the solution cooled to 0 C. Concentrated hydrochloric acid (45 ml) was added to produce a tan slurry. A solution of 1.89 g (0.027 mol) of sodium nitrite in 8 ml water was added dropwise with stirring, the resulting orange solution was stirred at 0 C. for 1 hour and then added in 6 portions to a mixture of 2.18 g (0.013 mol) of cupric chloride dihydrate and sulfur dioxide (6.3 g) in 33 ml of acetic acid and 6 ml of water at 0 C.The The

Molecular Weight:165.19
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:165.078978594
Monoisotopic Mass:165.078978594
Topological Polar Surface Area:52.3
Heavy Atom Count:12
Complexity:170
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes