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

HRID 1829175노트

반응식

HRID 1829175 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a4cb381dbae547459de75a0728aa2f4f
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07060836B2

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