Hydroxylamine → N-hydroxy-4-phenylbutanamide

Participants

Reaction Conditions

Reaction Steps

A solution of 4-phenylbutyric acid (10.0 g, 60.9 mmol) in anhydrous THF (180 mL) was added ethyl chloroformate (7.0 mL, 73.1 mmol) and triethylamine (11.1 mL, 79.2 mmol) at 0° C. The mixture was stirred at 0° C. for 15 min. The solid was filtered off. The filtrate was added to a freshly prepared methanolic hydroxylamine solution (63.0 mL, prepared by adding 6.34 g or 91.4 mmol of hydroxylamine hydrochloride to 30.0 mL of a stirred methanolic solution containing 5.13 g or 91.4 mmol of KOH at 0° C. for 15 min). The resulting mixture was stirred at room temperature for 30 min and evaporated in vacuo. The residue was purified by chromatography to give Compound 1 (6.4 g, 58%): mp>300° C.; NMR (400 MHz in CDCl3): δ 1.98 (m, 2H, PhCH2—CH2—CH2CONHOH), 2.13 (t, 2H, Ph-CH2—CH2CH2CONHOH), 2.64 (t, 2H, PhCH2CH2—CH2—CONHOH), 7.15 (d, 2H, Ar—H), 7.20 (t, 2H, Ar—H), 7.28 (m, 1H, Ar—H), 8.20 (br, 1H, NH).

Provenance & Evidence