4-Acetamidobenzaldehyde → HCID 4460275, compound

HRID 2214613Notes

Reaction equation

HRID 2214613 reaction equation
[C:1]([NH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].Cl.[O:14]([NH2:16])[CH3:15]>>[CH3:15][O:14][N:16]=[CH:9][C:8]1[CH:11]=[CH:12][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 739424-AcetamidobenzaldehydeHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 4460275HCID 4460275, compoundYield 98%

Procedure

Reaction of 4-acetamidobenzaldehyde with methoxylamine hydrochloride as described in the preparation of Compound 44-A gave the title oxime ether as a white solid (98% yield), (Sakamoto, T. et al., J. Org. Chem., 57, 1992, 3245–3248). 1HNMR indicated a 95:5 mixture of E- to Z-isomers. 1HNMR 400 MHz (CDCl3) δ (ppm): (E-isomer) 2.19 (3H, s, CH3), 3.96 (3H, s, OCH3), 7.22 (1H, broad s, NH), 7.53 (4H, m, aromatics), 8.01 (1H, s, CH).

Sources & evidence

ORD record
ord-2526d48a7f64481da1abb86e4f7a57ed
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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