Dimethylformamide → 3-cyano-N, 4-dimethylbenzamide

HRID 1830878Notes

Reaction equation

HRID 1830878 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([NH:7][CH3:8])=[O:6].[CH3:13][N:14](C=O)C>N.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C-]#N.[Zn+2].[C-]#N>[C:13]([C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([NH:7][CH3:8])=[O:6])#[N:14]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 196884403-iodo-N,4-dimethylbenzamide

Product 1

HCID 178597803-cyano-N, 4-dimethylbenzamide

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 18464838Ammonia ethyl acetateSolvent

Conditions

Temperature
120 °C

Procedure

3-Iodo-N, 4-dimethylbenzamide (772 mg), tetrakistriphenylphosphinepalladium (30 mg) and zinc cyanide (250 mg) were suspended in DMF (10 ml) under a nitrogen atmosphere, and the mixture was stirred at 120° C. for 12 hrs. The reaction mixture was diluted with 5% aqueous ammonia-ethyl acetate and the organic layer was washed with water and saturated brine. The organic layer was dried and concentrated, and the residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=2:1–0:1) for purification. The eluate was recrystallized from ethyl acetate-hexane to give the title compound (300 mg) as colorless powder crystals.

Workup

  1. washthe organic layer was washed with water and saturated brine
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customthe residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=2:1–0:1) for purification
  5. customThe eluate was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-16e76a07791f45ecb4f4c029730a3c4b
Source dataset
uspto-grants-2006_06
Patent number
US07067537B2

Reaction notes

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