HCID 520640, compound → N-Methoxy-1-(4-methoxyphenyl)methanamine

HRID 1836492Notes

Reaction equation

[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.C([BH3-])#N.[Na+]>>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][NH:3][O:2][CH3:1])=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 520640HCID 520640, compound

HCID 5003444Sodium cyanoborohydride

Product 1

HCID 21947441N-Methoxy-1-(4-methoxyphenyl)methanamineYield 96%

Procedure

Reduction of 4-methoxybenzaldehyde O-methyloxime with sodium cyanoborohydride as described in the preparation of compound 3-B gave the title hydroxylamine as a clear oil (96% yield). 1HNMR 400 MHz (CDCl3) δ (ppm): 3.49 (3H, s, OCH3), 3.79 (3H, s, OCH3), 3.98 (2H, s, NCH2), 5.62 (1H, broad s, NH), 6.86 (2H, m, aromatics), 7.25 (2H, m, aromatics). The hydrochloride salt was obtained as a white solid: mp 157-158° C. (dec.). Anal. calcd. for C9H13NO2—HCl: C, 53.03; H, 6.92; N, 6.87. Found: C, 53.14; H, 6.76; N, 6.80.

Sources & evidence

ORD record: ord-11a0634375ee473b80a5939ad807d701
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06777440B2

Reaction notes

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