4-Cyanobenzaldehyde o-methyloxime → HCID 21947408, compound
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+]>>[C:11]([C:8]1[CH:9]=[CH:10][C:5]([CH2:4][NH:3][O:2][CH3:1])=[CH:6][CH:7]=1)#[N:12]Participants
3
Procedure
Reduction of 4-cyanobenzaldehyde O-methyloxime with sodium cyanoborohydride as described in the preparation of compound 3-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-4d9ac133d2fb42a5a4ae68070674cf41
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06777440B2
Reaction notes
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