Hydrochloric Acid → N-(2-Chloro-4-fluorophenyl)-2-(hydroxyimino)-acetamide

Participants

Reaction Steps

A solution of chloral hydrate (6.25 g, 37.8 mmol), sodium sulfate decahydrate (48.3 g, 340 mmol) and water (100 mL) was added to a stirred solution of 2-chloro-4-fluoroaniline (5.0 g, 34 mmol), hydroxylamine hydrochloride (9.19 g, 130 mmol), water (50 mL) and concentrated hydrochloric acid (3 mL). The reaction mixture was heated under reflux for 1 h, cooled to room temperature, stirred for 16 h and filtered. The filter-cake was recrystallised (methanol-water) to give the product (5.58 g, 75% yield) as a pale brown solid: IR νmax (Nujol)/cm−1 1655, 1613, 1536, 1267, 1191, 1021, 853 and 558; NMR δH (400 MHz, DMSO-d6) 7.20-7.29 (1H, m), 7.51-7.57 (1H, m), 7.78-7.84 (1H, m), 9.61 (1H, s) and 12.36 (1H, s).

Provenance & Evidence