Pyridine → 1-Methyl-2-oxo-1,2-dihydropyridine-4-carbonitrile

HRID 1829175Notes

Reaction equation

HRID 1829175 reaction equation
C(Cl)(=O)C(Cl)=O.CN(C)C=O.[CH3:12][N:13]1[CH:18]=[CH:17][C:16]([C:19]([NH2:21])=O)=[CH:15][C:14]1=[O:22].N1C=CC=CC=1>C(#N)C.O>[CH3:12][N:13]1[CH:18]=[CH:17][C:16]([C:19]#[N:21])=[CH:15][C:14]1=[O:22]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 8206011-Methyl-2-oxo-1,2-dihydropyridine-4-carboxamide

Product 1

HCID 111709951-Methyl-2-oxo-1,2-dihydropyridine-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

Oxalyl chloride (250 μl, 2.87 mmol) was added to an ice-cooled solution of N,N-dimethylformamide (243 μl, 3.14 mmol) in acetonitrile (3 ml). A suspension of 1-methyl-2-oxo-1,2-dihydro-4-pyridinecarboxamide (J.O.C. 24; 1959; 196) (201.5 mg, 1.32 mmol) and pyridine (470 μl, 5.82 mmol) in acetonitrile (20 ml) was added to the resulting white suspension, and the mixture stirred at room temperature for 18 hours. The mixture was diluted with water (20 ml), and extracted with ethyl acetate (2×100 ml). The combined organic solutions were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel using ethyl acetate:pentane (75:25), then dichloromethane:methanol (90:10) as eluants, to afford the title compound as a pale yellow solid, 112.3 mg.

Workup

  1. additionwas added to the resulting white suspension
  2. extractionextracted with ethyl acetate (2×100 ml)
  3. washThe combined organic solutions were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-a4cb381dbae547459de75a0728aa2f4f
Source dataset
uspto-grants-2006_06
Patent number
US07060836B2

Reaction notes

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