Hydroxylamine → N-Hydroxy-4-phenylbutanamide

Temperature

0 °C

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).

1. filtrationThe solid was filtered off
2. stirringThe resulting mixture was stirred at room temperature for 30 min
3. customevaporated in vacuo
4. customThe residue was purified by chromatography

ORD record

ord-117ca5f9af224d6a88adb078cf828202

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08242282B2