HCID 4460275, compound → HCID 21947356, compound

HRID 1836511Notes

Reaction equation

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

Participants

Reactant 2

HCID 4460275HCID 4460275, compound

HCID 5003444Sodium cyanoborohydride

Product 1

HCID 21947356HCID 21947356, compound

Procedure

Reduction of 4-acetamidobenzaldehyde O-methyloxime with sodium cyanoborohydride as described in the preparation of compound 3-B gave the title hydroxylamine as a waxy solid (100% yield). 1HNMR 400 MHz (CDCl3) δ (ppm): 2.16 (3H, s, CH3), 3.49 (3H, s, OCH3), 4.00 (2H, s, NCH2), 7.26 (1H, broad s, NH), 7.29 (2H, m, aromatics), 7.46 (2H, m, aromatics). The hydrochloride salt was obtained as a white solid: mp 186-188° C. (dec.). Anal. calcd. for C10H14N2O2—HCl—H2O: C, 50.87; H, 6.66; N, 11.87. Found: C, 50.77; H, 6.44; N, 12.16.

Sources & evidence

ORD record: ord-cbe84d61254e4e6aa41e394c5b1c000c
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06777440B2

Reaction notes

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