Dimethylformamide → 3-Acetylbenzamide

Participants

Reaction Conditions

Reaction Steps

General Procedure FF: Into DMF (11 ml, 140 mmol) solution of 3-acetylbenzoic acid (706 mg, 4.30 mmol) which was cooled in ice/water bath was added triethylamine (602 μl, 4.30 mmol) followed by addition of ethyl chloroformate (424 μl, 4.30 mmol) dropwise in 5 min under an atmosphere of nitrogen. The mixture was stirred at 0° C. for 30 min and then at rt for 30 min. Ammonium hydroxide (28% aq. solution; 1.15 ml) was added, and the mixture was stirred at rt for 3 h. After that time, the mixture was poured into ice/water, extracted with EtOAc (3×50 ml). The extracts were washed with water (2×30 ml), brine (30 ml), dried over MgSO4, filtered and concentrated in vacuo, giving the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ=2.66 (s, 3H), 7.58 (dt, J=0.4 & 8.0 Hz, 1H), 8.05 (md, J=8.0 Hz, 1H), 8.12 (md, J=8.0 Hz, 1H), 8.38-8.41 (m, 1H). MS (ES+): m/z 164.10 [MH+]. HPLC: tR=1.89 min (polar—5 min, ZQ3).

Provenance & Evidence