4-Carbomethoxybenzaldehyde o-methyloxime → HCID 21947509, compound

HRID 2214624Notes

Reaction equation

HRID 2214624 reaction equation
[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=1.C([BH3-])#N.[Na+]>>[CH3:14][O:13][C:11](=[O:12])[C:8]1[CH:9]=[CH:10][C:5]([CH2:4][NH:3][O:2][CH3:1])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6063154-Carbomethoxybenzaldehyde o-methyloximeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 21947509HCID 21947509, compoundYield 53%

Procedure

Reduction of 4-carbomethoxybenzaldehyde O-methyloxime with sodium cyanoborohydride as described in the preparation of Compound 44-B gave the title hydroxylamine as an oil (53% yield). The hydrochloride salt was obtained as a white solid: mp 166–169° C. 1HNMR 400 MHz (DMSO-d6) δ (ppm): 3.75 (3H, s, OCH3), 3.86 (3H, s, OCH3), 4.39 (2H, s, NCH2), 7.65 (2H, d, aromatics), 7.97 (2H, d, aromatics). Anal. calcd for C10H13NO3—HCl: C, 51.84; H, 6.09; N, 6.04. Found: C, 51.74; H, 6.01; N, 5.50.

Sources & evidence

ORD record
ord-0d0aa537b96d43958f50e6b13288c805
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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