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

HRID 1087190Notes

Reaction equation

HRID 1087190 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

5

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 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).

Workup

  1. temperaturerefluxed for 11 hours
  2. stirringThe mixture was stirred
  3. filtrationfiltered
  4. customThe filtrate was separated
  5. customthe organic layer was dried
  6. customevaporated
  7. customThe oily residue was purified by column chromatography on silica gel (200 g)
  8. washeluting with a mixture of toluene and ethyl acetate (20:1)

Sources & evidence

ORD record
ord-0f93b2f3423b45ebbe194eaa33773e46
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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