Methylamine → N-methyl-3-nitrobenzamide

Participants

Reaction Steps

In a dry flask 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 (500 mL) and extracted with water three times (100 mL). The organic layer was dried with sodium sulfate, filtered, and concentrated in vacuo. The crude solid (6.38 g, 94%) was used with further purification. 1H NMR (300 MHz, CDCl3), δ: 8.84 (bs, 1H), 8.67 (m, 1H), 8.37 (dd, J=8, J′=2, 1H), 8.28 (d, J=7, 1H), 7.78 (dd, J=8, J′=7, 1H), 2.83 (m, 3H). MS (ESI), m+/z: (M+H)+=181.

Provenance & Evidence