Hydroxylamine → Veratraldehyde

HRID 2301290Notes

Reaction equation

HRID 2301290 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH:6]=[CH:7][C:8]#[N:9].N[OH:16].[CH2:17]([OH:19])[CH3:18].O>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH:6]=[CH:7][C:8]#[N:9].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH:6]=[O:19].[C:8]([CH2:18][C:17]([OH:16])=[O:19])#[N:9]

Participants

7

Reactant 3

HCID 787HydroxylamineHCID 978723-(3,4-Dimethoxyphenyl)-2-propenenitrileHCID 19096565Water ethanol

Product 3

HCID 8419VeratraldehydeHCID 9740Cyanoacetic acidHCID 978723-(3,4-Dimethoxyphenyl)-2-propenenitrile

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3,4-Dimethoxy-cinnamic acid amidoxime used as starting material was prepared by the reaction of 3,4-dimethoxycinnamonitrile with hydroxylamine under the usual conditions in ethanol-water solution. The 3,4-dimethoxycinnamonitrile was obtained from 3,4-dimethoxybenzaldehyde with cyanoacetic acid in pyridine solution by literature method (J. Am. Chem. Soc. 65, 22(1943)).

Sources & evidence

ORD record
ord-ec8afbf4ba6c45a6bf4fb617dd6fc30e
Source dataset
uspto-grants-2002_12
Patent number
US06500823B1

Reaction notes

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