Sodium cyanoborohydride → HCID 12146891, compound

HRID 1836482Notes

Reaction equation

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

Participants

Reactant 2

HCID 5003444Sodium cyanoborohydride

HCID 73855563HCID 73855563, compound

Product 1

HCID 12146891HCID 12146891, compoundYield 74%

Procedure

Reduction of 4-fluorobenzaldehyde O-ethyloxime with sodium cyanoborohydride as described in the preparation of compound 3-B gave the title hydroxylamine as a clear oil after chromatography (74% yield). 1HNMR 400 MHz (C6D6) δ (ppm): 1.13 (3H, t, J=7.1 Hz, CH3), 3.70 (2H, q, J=7.1 Hz, OCH2), 3.78 (2H, d, J=5.4 Hz, NCH2), 5.20 (2H, broad t, NH), 6.89 (2H, m, aromatics), 7.09 (2H, m, aromatics). Anal. calcd for C9H12FNO: C, 63.88; H, 7.14; N, 8.27. Found: C, 63.68; H, 7.08; N, 8.46.

Sources & evidence

ORD record: ord-fa9100df79434a9682eab6b025ad3dbc
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06777440B2

Reaction notes

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