Sodium cyanoborohydride → HCID 21947464, compound
Reaction equation
[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([C:12]#[N:13])[CH:6]=1.C([BH3-])#N.[Na+]>>[C:12]([C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[F:11])[CH2:4][NH:3][O:2][CH3:1])#[N:13]Participants
3
Procedure
Reduction of 3-cyano-4-fluorobenzaldehyde O-methyloxime with sodium cyanoborohydride as described in the preparation of compound 3-B gave the title hydroxylamine as a clear oil after chromatography on silica gel (elution hexane-ethyl acetate 8: 2) (73% yield). 1HNMR 400 MHz (CDCl3) δ (ppm): 3.46 (3H, s, OCH3), 4.02 (2H, s, NCH2), 7.18 (1H, t, aromatic), 7.58-7.66 (2H, m, aromatics). The hydrochloride salt was obtained as a white solid: mp 152-158° C. Anal. calcd for C9H9FN2O—HCl: C, 49.89; H, 4.65; N, 12.93. Found: C, 50.04; H, 4.64; N, 12.84.
Sources & evidence
- ORD record
- ord-b093001628e14729905836fd2b6a4b16
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06777440B2
Reaction notes
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