Triethylamine → N-methyl-N-methyloxy-2-benzyloxycarbonylamino-5-hydroxybenzamide

Participants

Reaction Steps

2-Benzyloxycarbonylamino-5-hydroxybenzoic acid (6.0 g) and N,O-dimethylhydroxylamine hydrochloride (2.5 g) were dissolved in methylenb chloride (80 ml). To the solution were added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (4.6 g) and triethylamine (5 ml). The mixture was stirred for 2 hours at room temperature. The reaction mixture was concentrated under reduced pressure. To the concentrate was added water, which was subjected to extraction with ethyl acetate (200 ml). The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by means of a silica gel column chromatography to give N-methyl-N-methyloxy-2-benzyloxycarbonylamino-5-hydroxybenzamide as a yellow oily product (5.0 g).

Provenance & Evidence