Hydroxyamine hydrochloride → HCID 73988975, compound

Participants

Reaction Steps

A solution of the product of Example 80 (0.40 g, 0.80 mmol), hydroxylamine hydrochloride (0.16 g, 2.4 mmol) and sodium acetate (0.19 g, 2.4 mmol) in ethanol (60 ml) was heated at reflux for 16 hours and stirred at room temperature for 32 hours. The mixture was evaporated in vacuo and extracted with ethyl acetate (50 ml). The organic phase was washed with brine (sat. 40 ml), dried (magnesium sulfate) and evaporated in vacuo. The crude product was chromatographed on silica, eluting with 20-28% ethyl acetate/isohexane to give the oxime (0.36 g, 87%). 1H NMR (DMSO, 360 MHz): 1.49 (2H, bt, J=12.3), 1.82 (2H, bd, J=14.0), 2.40 (2H, bt, J=13.8), 2.50-2.60 (2H, m), 3.64 (1H, bs), 7.08-7.20 (2H, m), 7.28-7.34 (1H, m), 7.37 (2H, d, J=8.3), 7.72 (2H, d, J=8.3), 8.24 (1H, s), 9.76 (0.5H, d, J=5.9), 11.74 (0.5H, s)

Provenance & Evidence