4-Cyanobenzaldehyde → 4-Cyanobenzaldehyde o-methyloxime

HRID 2214608Notes

Reaction equation

HRID 2214608 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)#[N:2].Cl.[O:12]([NH2:14])[CH3:13]>>[CH3:13][O:12][N:14]=[CH:7][C:6]1[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

3

Reactant 2

HCID 660424-CyanobenzaldehydeHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 5947614-Cyanobenzaldehyde o-methyloximeYield 96%

Procedure

Reaction of 4-cyanobenzaldehyde with methoxylamine hydrochloride as described in the preparation of Compound 44-A gave the title oxime ether as a white solid (96% yield), (Gordon, M. S. et al., J. Org. Chem., 49, 1984, 97–100). 1HNMR indicated a 95:5 mixture of E- to Z-isomers. 1HNMR 400 MHz (CDCl3) δ (ppm): (E-isomer) 4.02 (3H, s, OCH3), 7.07 (4H, m, aromatics), 8.06 (1H, s, CH).

Sources & evidence

ORD record
ord-a3b1bc365b874773b4c23701d2611a3c
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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