Acetic Anhydride → N-(1-(4-bromopyridin-2-yl)ethyl)acetamide

Participants

Reaction Steps

To a solution of 1-(4-bromopyridin-2-yl)ethanamine (2.3 g, 11.44 mmol) in chloroform (30 mL) was added acetic anhydride (2.16 mL, 22.88 mmol) dropwise at 0° C. The reaction was then quenched with ice water (40 mL) and extracted with chloroform (2×50 mL). The organic extracts were combined, then washed with 1M NaOH (50 mL), dried over Na2SO4, concentrated, and purified by column chromatography (gradient 0 to 5% MeOH/DCM) to afford the product. 1H NMR (400 MHz, CDCl3) δ 8.35 (d, J=5.3 Hz, 1H), 7.42 (s, 1H), 7.36 (dd, J=5.3, 1.7 Hz, 1H), 6.71 (br s, 1H), 5.10 (p, J=7.0 Hz, 1H), 2.02 (s, 3H), 1.45 (d, J=6.8 Hz, 3H).

Provenance & Evidence