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

HRID 1829175ノート

反応式

HRID 1829175 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a4cb381dbae547459de75a0728aa2f4f
出典データセット
uspto-grants-2006_06
特許番号
US07060836B2

反応ノート

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