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

HRID 1836514Notes

Reaction equation

[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1.C([BH3-])#N.[Na+]>>[CH3:1][O:2][NH:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1

Participants

Reactant 2

HCID 520639O-Methyl-p-tolualdoxime

HCID 5003444Sodium cyanoborohydride

Product 1

HCID 23499551n-(4-Methylbenzyl)-o-methyl-hydroxylamineYield 76%

Procedure

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.

Sources & evidence

ORD record: ord-914a7f4e32d34a8f9f068ab474974203
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06777440B2

Reaction notes

Loading…