Hydroxyamine hydrochloride → HCID 178426650, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2.5 g (10.2 mmol) of tert-butyl 3-(3-methyl-4-cyanophenyl) propionate (from Step B), 0.85 g (12.2 mmol) of hydroxylamine hydrochloride and 2.57 g (30.6 mmol) of sodium bicarbonate in 30 mL of methanol was heated in a sealed tube at 100° C. for 16 h. The reaction mixture was cooled to rt, then concentrated. The residue was partitioned between EtOAc (50 mL) and water (50 mL). The organic layer was separated and washed with sat'd NaCl (3×50 mL), dried over MgSO4, and concentrated. Chromatography on a Biotage 40M cartridge using 7:3 v/v hexanes/EtOAc as the eluant afforded 1.65 g (58%) of the title compound as a white solid: 1H NMR (500 MHz, CDCl3) δ 1.45 (s, 9H), 2.40 (s, 3H), 2.54 (t, J=7.8, 2H), 2.90 (t, J=7.8, 2H), 5.05 (s, 2H), 7.04 (d, J=7.8, 1H), 7.08 (s, 1H), 7.27 (d, J=7.8, 1H).

Provenance & Evidence