O-Methyl-p-tolualdoxime → n-(4-Methylbenzyl)-o-methyl-hydroxylamine

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Reaction Steps

Reduction of 4-methylbenzaldehyde O-methyloxime with sodium cyanoborohydride as described in the preparation of compound 3-B gave the title hydroxylamine as a clear oil (76% yield): bp 70-80° C./3.5 torr (bulb to bulb distillation, air bath temperature). 1HNMR 400 MHz (CDCl3) δ (ppm): 2.36 (3H, s, CH3), 3.54 (3H, s, OCH3), 4.04 (2H, s, NCH2), 5.7 (broad, NH), 7.17 (2H, d, J=8.1 Hz, aromatics), 7.26 (2H, d, J=8.1 Hz, aromatics). The hydrochloride salt was obtained as a white solid: mp 162-164° C. Anal. calcd for C9H13NO—HCl: C, 57.60; H, 7.51; N, 7.46. Found: C, 57.87; H, 7.45; N, 7.25.

Provenance & Evidence