Sodium cyanoborohydride → n-(2-Isopropoxy-benzyl)-o-methyl-hydroxylamine

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Reduction of 2-isopropoxy-benzaldehyde O-methyloxime with sodium cyanoborohydride as described in the preparation of compound 1-B gave the title hydroxylamine as a clear oil after chromatography on silica gel (elution hexane-ethyl acetate 8:2) (83% yield). 1HMR 400 MHz (CDCl3) δ (ppm): 1.35 (6H, d, J=6.1 Hz, CH3), 3.56 (3H, s, OCH3), 4.07 (2H, broad s, NCH2), 4.59 (1H, m, CH), 6.08 (1H, broad s, NH), 6.86-6.91 (2H, m, aromatics), 7.20-7.24 (2H, m, aromatics). The hydrochloride salt was obtained as a white solid: mp 90° C. Anal. calcd for C11H17NO2—HCl: C, 57.02; H, 7.83; N, 6.04. Found: C, 56.93; H, 7.64; N, 5.96

Provenance & Evidence