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

HRID 626185ノート

反応式

HRID 626185 の反応式
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]

参加物

5

反応物 4

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

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-30b169dd51044ba589aa92a4edfcf8e9
出典データセット
uspto-grants-2016_04
特許番号
US09309211B2

反応ノート

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