Dimethylformamide → Methyl 1-methyl-2-oxo-1,2-dihydropyridine-4-carboxylate

HRID 626185노트

반응식

HRID 626185 반응식
O=C1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=CN1.[H-].[Na+].[CH3:13]I.[CH3:15][N:16]([CH:18]=[O:19])[CH3:17]>>[CH3:15][N:16]1[CH:17]=[CH:5][C:6]([C:8]([O:10][CH3:13])=[O:9])=[CH:7][C:18]1=[O:19]

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2807562-Hydroxyisonicotinic Acid

생성물 1

HCID 819408Methyl 1-methyl-2-oxo-1,2-dihydropyridine-4-carboxylate수율 25%

실험 절차

To a solution of 2-oxo-1,2-dihydropyridine-4-carboxylic acid (5 g, 1.0 eq) in 100 mL DMF was added 60% NaH (4.3 g, 3.0 eq) slowly at 0° C., and the mixture was stirred for 30 min at rt. Then CH3I (15.3 g, 3.0 eq) was added dropwise at 0° C. After the reaction was stirred at rt overnight, the reaction mixture was quenched with water and extracted with EtOAc. The extract was dried, concentrated, and purified by column chromatography to give the desired product (1.5 g, 25% yield). 1H NMR (400 MHz, CDCl3) δ 7.34 (d, J=7.2 Hz, 1H), 7.21 (d, J=2.0 Hz, 1H), 6.65 (dd, J=6.8 Hz, 2.0 Hz, 1H), 3.91 (s, 3H), 3.57 (s, 3H).

후처리

  1. stirringAfter the reaction was stirred at rt overnight
  2. customthe reaction mixture was quenched with water
  3. extractionextracted with EtOAc
  4. customThe extract was dried
  5. concentrationconcentrated
  6. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-30b169dd51044ba589aa92a4edfcf8e9
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309211B2

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