Benzonitrile → N-Benzylacetamide

HRID 580082Notes

Reaction equation

[C:1](#[N:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[C:13](=[O:15])[CH3:14])(=[O:11])C>>[CH:1](=[N:8][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:13]([NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:15])[CH3:14]

Participants

Reactant 2

HCID 7505Benzonitrile

HCID 7918Acetic Anhydride

Product 2

HCID 11500N-Benzylacetamide

HCID 12143(Z)-Benzaldehyde oxime

Procedure

Also, by reaction of benzaldoxime with acetic anhydride benzaldoxime acetate is formed, which is then reduced, thus benzylamine being obtained with 91% (K. W. Rosenmund et al, Ber., 56 2258-2262 (1923)). These processes of reducing benzonitrile or benzaldoxime in the acetic anhydride solvent comprise isolating N-acetylbenzylamine and hydrolysing same to obtain benzylamine.

Sources & evidence

ORD record: ord-68765ddf77944458a5757ad984f70f48
Source dataset: uspto-grants-1988_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04751328

Reaction notes

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