4-Cyanobenzaldehyde o-methyloxime → HCID 21947408, compound

HRID 2214609Notes

Reaction equation

HRID 2214609 reaction equation
[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[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]([C:11]#[N:12])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 5947614-Cyanobenzaldehyde o-methyloximeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 21947408HCID 21947408, compoundYield 75%

Procedure

Reduction of 4-cyanobenzaldehyde O-methyloxime with sodium cyanoborohydride as described in the preparation of Compound 44-B gave the title hydroxylamine as a clear oil (75% yield). 1HNMR 400 MHz (CDCl3) δ (ppm): 3.48 (3H, s, OCH3), 4.09 (2H, s, NCH2), 7.48 (2H, m, aromatics), 7.63 (2H, m, aromatics). The hydrochloride salt was obtained as a white solid: mp 168° C. (dec.). Anal. calcd. for C9H10N2O—HCl: C, 54.41; H, 5.58; N, 14.10. Found: C, 54.44; H, 5.62; N, 13.94.

Sources & evidence

ORD record
ord-18ad0e10db0e4763a2e8cde6ff13ccd0
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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