Dimethylformamide → 2-(3-Cyano-4-nitrophenyl)-2-methyl-1,3-dioxolane

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([C:11]2([CH3:16])[O:15][CH2:14][CH2:13][O:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].C(=O)(O)[O-].[Na+].C(OCC)(=O)C.[CH3:28][N:29](C)C=O>>[C:28]([C:2]1[CH:3]=[C:4]([C:11]2([CH3:16])[O:15][CH2:14][CH2:13][O:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])#[N:29]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 8857Ethyl Acetate

HCID 516892Sodium Bicarbonate

HCID 100374432-(3-Chloro-4-nitrophenyl)-2-methyl-1,3-dioxolane

Product 1

HCID 100142372-(3-Cyano-4-nitrophenyl)-2-methyl-1,3-dioxolane

Procedure

A mixture of 2-(3-chloro-4-nitrophenyl)-2-methyl-1,3-dioxolane (9.8 g) and cuprous cyanide (4.0 g) in N,N-dimethylformamide (20 ml) was stirred and refluxed for 11 hours. An aqueous solution of sodium bicarbonate (200 ml) and ethyl acetate (100 ml) were added to the reaction mixture. The mixture was stirred and filtered. The filtrate was separated and the organic layer was dried and evaporated. The oily residue was purified by column chromatography on silica gel (200 g) eluting with a mixture of toluene and ethyl acetate (20:1) to give yellow plates of 2-(3-cyano-4-nitrophenyl)-2-methyl-1,3-dioxolane (4.6 g).