Sodium cyanoborohydride → HCID 22485646, compound
Reaction equation
[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([F:12])[CH:6]=1.C([BH3-])#N.[Na+]>>[F:12][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[CH3:11])[CH2:4][NH:3][O:2][CH3:1]Participants
3
Procedure
Reduction of 3-fluoro-4-methyl-benzaldehyde O-methyloxime with sodium cyanoborohydride as described in the preparation of compound 1-B gave the title hydroxylamine as a clear oil after chromatography on silica gel (elution hexane-ethyl acetate 8: 2) (57% yield). 1HNMR 400 MHz (CDCl3) δ (ppm): 2.25 (3H, broad s, CH3), 3.50 (3H, s, OCH3), 3.99 (2H, broad s, NCH2), 5.71 (1H, broad, NH), 7.01 (2H, m, aromatics), 7.13 (1H, m, aromatic). The hydrochloride salt was obtained as a white solid: mp 140-142° C. Anal. calcd for C9H12FNO—HCl: C, 52.56; H, 6.37; N, 6.81. Found: C, 52.63; H, 6.30; N, 6.78.
Sources & evidence
- ORD record
- ord-d2c45d925eee4e158ec4a5a372f63fc5
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06890942B2
Reaction notes
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