Acetonitrile → 2-Methoxybenzoylacetonitrile

HRID 986826Notes

Reaction equation

HRID 986826 reaction equation
CO[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH3:11].[NH2-].[Na+].[C:15](#[N:17])[CH3:16]>>[CH3:11][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([CH2:16][C:15]#[N:17])=[O:12]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 24533Sodium amideHCID 61151Methyl 2-Methoxybenzoate

Product 1

HCID 49627502-MethoxybenzoylacetonitrileYield 84%

Procedure

In agreement with this data the condensation of 2-methoxybenzoic acid methyl ester with acetonitrile using sodamide/liquid ammonia gives 2-methoxybenzoylacetonitrile in 84% yield, in contrast this same reaction using sodium hydride in benzene only leads to a 27.4% reaction yield. (Kawase, Bull, Chem. Soc. Japan, Vol. 35 (1962), pages 1869-1871.)

Sources & evidence

ORD record
ord-5b875bdeebb3472cbd0b841bc53a3f2e
Source dataset
uspto-grants-1987_12
Patent number
US04716237

Reaction notes

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