O-Methylhydroxylamine hydrochloride → 2-Fluoro-5-[(methoxyimino)methyl]benzonitrile

HRID 1836498Notes

Reaction equation

HRID 1836498 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]=1

Participants

3

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 27695822-Fluoro-5-formylbenzonitrile

Product 1

HCID 738555792-Fluoro-5-[(methoxyimino)methyl]benzonitrile

Procedure

Reaction of 3-cyano-4-fluorobenzaldehyde with methoxylamine hydrochloride as described in the preparation of compound 3-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- and 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-06909647446447a2b21c7380c4356f34
Source dataset
uspto-grants-2004_08
Patent number
US06777440B2

Reaction notes

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