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

HRID 626185Notes

Reaction equation

HRID 626185 reaction equation
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]

Participants

5

Reactant 4

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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-30b169dd51044ba589aa92a4edfcf8e9
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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