Dimethylformamide → HCID 10035118, compound

HRID 2379805Notes

Reaction equation

HRID 2379805 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([O:9][CH2:10][C:11]1[N:16]=[C:15]([C:17]([NH2:19])=O)[CH:14]=[CH:13][CH:12]=1)(=[O:8])[CH3:7].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[C:6]([O:9][CH2:10][C:11]1[N:16]=[C:15]([C:17]#[N:19])[CH:14]=[CH:13][CH:12]=1)(=[O:8])[CH3:7]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 10330249HCID 10330249, compound

Product 1

HCID 10035118HCID 10035118, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Phosphorus oxychloride (86.9 ml) was dropwise added to a mixture of 6-acetoxymethyl-2-pyridinecarboxamide (93.0 g) and N,N-dimethylformamide (74.2 ml) in ethyl acetate (930 ml) under ice-cooling with stirring and the mixture was stirred at ambient temperature for 4 hours. The reaction mixture was added to a water and adjusted to pH 8 with potassium carbonate. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated to give 6-acetoxymethyl-2-cyanopyridine (84.0 g) as an oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at ambient temperature for 4 hours
  3. washThe separated organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-9c9560dde1f4498bb4e6a9c5590d7b81
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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