o-Benzylbenzoic acid → 2-benzyl-N-methylbenzamide

Participants

Reaction Steps

To a stirred solution of α-phenyl-o-toluic acid (2.0 g, 9.43 mmol) in methylene chloride (500 mL) at room temperature under argon was added by dropwise addition a solution of oxalyl chloride (0.988 mL, 11.3 mmol) in methylene chloride (50 mL). N,N-Dimethylformamide (10 drops) were added and the contents of the reaction flask were stirred 1.5 h. Solvent was removed in vacuo and methylene chloride (100 mL) and methylamine hydrochloride (950 mg, 14.1 mmol) was added. With ice-bath cooling a solution of N,N-diisopropylethylamine (4.10 mL, 23.6 mmol) in methylene chloride (10 mL) was added dropwise. Saturated sodium bicarbonate was added and the resulting mixture extracted with methylene chloride (3×). The combined organic extracts were dried with sodium sulfate (anh.). Filtration followed by removal of the solvent in vacuo gave a solid which after trituration with ether afforded N-Methyl-2-(phenylmethyl) benzamide (974 mg, 4.23 mol, 46%). MS [M+H]+226

Provenance & Evidence