Dimethylformamide → 3-Oxocyclohexane-1-carbonitrile

HRID 1269947Notes

Reaction equation

HRID 1269947 reaction equation
[Cl-].[NH4+].[C-]#N.[K+].[C:6]1(=[O:12])[CH2:11][CH2:10][CH2:9][CH:8]=[CH:7]1.[CH3:13][N:14](C)C=O>O>[C:13]([CH:8]1[CH2:9][CH2:10][CH2:11][C:6](=[O:12])[CH2:7]1)#[N:14]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 9032Potassium CyanideHCID 135942-Cyclohexen-1-oneHCID 25517Ammonium Chloride

Product 1

HCID 128412163-Oxocyclohexane-1-carbonitrileYield 5.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Under a nitrogen atmosphere, ammonium chloride (4.17 g, 0.078 mol) and potassium cyanide (6.77 g, 0.104 mol) were added to a solution of 2-cyclohexen-1-one (5.0 g, 0.052 mol) in a 15%-aqueous N,N-dimethylformamide solution (60 ml) at room temperature, and the resulting mixture was heated to 100° C. After 3 hours, the reaction solution was poured into water and extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 1-cyanocyclohexan-3-one (345.4 mg, 5.4%).

Workup

  1. extractionextracted with chloroform
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. customThe organic layer dried
  4. concentrationwas concentrated under reduced pressure
  5. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9c039b0e664944b2b97c537fa513262f
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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