Hydroxylamine → Tert-butyl[{3-[amino(hydroxyimino)methyl]benzyl}(methyl)amino]acetate

Participants

Reaction Steps

To a solution of tert-butyl [(3-cyanobenzyl)(methyl)amino]acetate (9 g, 34.6 mmol) in ethanol (60 mL) under N2, was added hydroxylamine (6 g, 178.8 mmol) in one portion. After being stirred at RT for 12 h, the reaction mixture was concentrated under reduced pressure to afford a colorless oil. It was triturated in diisopropyl ether, affording the title product as a white solid that was filtrated and dried under vacuo (8.5 g, 84%). 1H NMR (DMSO-d6, 300 MHz) δ 9.57 (1H, s), 7.59 (1H, s), 7.52-7.53 (1H, m), 7.29-7.31 (2H, m), 5.75 (2H, s), 3.61 (2H, s), 3.15 (2H, s), 2.23 (3H, s), 1.41 (9H, s). LC/MS (Method A): 294.0 (M+H)+. HPLC (Method B) Rt 3.31 min (Purity: 97.5%).

Provenance & Evidence