Hydrochloric Acid → 2-(Hydroxyimino)-N-[2-(propan-2-yl)phenyl]acetamide

Participants

Reaction Steps

In a 2-1 round-bottomed flask are placed water (1000 ml), followed by chloral hydrate (49 g, 0.30 mol), anhydrous sodium sulfate (225 g), 2-isopropylaniline (50 g, 0.37 mol), concentrated hydrochloric acid (22 ml, 0.26 mol), hydroxylamine hydrochloride (57 g, 0.81 mol). The solution was boiled for 3 hr, cooled, quenched with water, and extracted with ethyl acetate. The extracts were dried over MgSO4, and evaporated. The residue was purified by elution from a silica gel column with hexane/EtOAc (7:3) to afford the product (26.7 g, 35%). 1H NMR (300 MHz, CDCl3) δ 8.28 (br, NH), 7.88 (dd, 1H), 7.82 (b, NOH), 7.63 (s, N═CH), 7.24 (m, 3H), 3.04 (m, 1H), 1.27 (d, 6H); ESI (+) MS m/e=207 (MH+), ESI (−) MS m/e=205 (MH−).

Provenance & Evidence