O-Methylhydroxylamine hydrochloride → 3-Cyano-4-fluorobenzaldehyde o-methyloxime
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[F:11])[CH:6]=O)#[N:2].Cl.[O:13]([NH2:15])[CH3:14]>>[CH3:14][O:13][N:15]=[CH:6][C:5]1[CH:8]=[CH:9][C:10]([F:11])=[C:3]([C:1]#[N:2])[CH:4]=1Participants
3
Procedure
Reaction of 3-cyano-4-fluorobenzaldehyde with methoxylamine hydrochloride as described in the preparation of Compound 44-A gave the title oxime ether as a clear oil after chromatography on silica gel (elution hexane-ethyl acetate 8:2) (94% yield). 1HNMR indicated a 93:7 mixture of E- to Z-isomers. 1HNMR 400 MHz (CDCl3) δ (ppm): (E-isomer) 4.02 (3H, s, OCH3), 7.26 (1H, m, aromatic), 7.85 (2H, m, aromatics), 8.03 (1H, s, CH).
Sources & evidence
- ORD record
- ord-e1398278f1b642e7bc98c898588ffde6
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07109186B2
Reaction notes
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