Methylamine → N-methyl-3-nitrobenzamide

Participants

Reaction Steps

3-Nitrobenzoyl chloride (7.00 g, 37.7 mmol) was dissolved in tetrahydrofuran (300 mL) and methylamine (41.5 mL of a 2.0 M solution in tetrahydrofuran, 82.9 mmol) was added. The reaction mixture was stirred for 2 hours. The reaction mixture was diluted with ethyl acetate and washed three times with water. The organic layer was dried over sodium sulfate and concentrated to provide a solid (6.38 g, 94%) which was used without further purification. 1H NMR (300 MHz, CDCl3), δ8.84 (bs, 1H), 8.67 (m, 1H), 8.37 (dd, J=8, 2 Hz, 1H), 8.28 (d, J=7 Hz, 1H), 7.78 (dd, J=8, 7 Hz, 1H), 2.83 (m, 3H). Mass spec (ES+) m+/z 181 (M+H+).

Provenance & Evidence