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

HRID 626185Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 626185
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]

Komponenten

5

Edukt 4

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

Produkt 1

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

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-30b169dd51044ba589aa92a4edfcf8e9
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309211B2

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