1,1-Dimethylhydrazine → 1,3-Benzenedicarboxylic acid, monomethyl ester, 2,2-dimethylhydrazide

Participants

Reaction Steps

To the acid 3-(methoxycarbonyl)benzoic acid (253 mg, 1.40 mmol) in CH2Cl2 at rt, EDCI (312 mg, 1.64 mmol) and HOBT (189 mg, 1.40 mmol) were added and stirred at rt for 20 min. To that mixture, N,N-dimethyl hydrazine was added followed by DIPEA (404 mg, 14.0 mmol). Reaction mixture was stirred at rt for 16 h. Then reaction mixture was diluted with chloroform, washed with water, brine and dried. Crude residue was purified by column chromatography to yield 60% of methyl 3-(2,2-dimethylhydrazinecarbonyl)benzoate.

Provenance & Evidence