Water → Benzyl 1-benzyl-2-oxo-1,2-dihydropyridine-4-carboxylate

HRID 1361896Notes

Reaction equation

O=[C:2]1[CH:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][NH:3]1.[C:11](=[O:14])([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH2:25]>CN(C=O)C>[CH2:4]([N:3]1[CH:2]=[CH:7][C:6]([C:8]([O:10][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:25])=[CH:5][C:11]1=[O:14])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 50 °C

Procedure

2-Oxo-1,2-dihydropyridine-4-carboxylic acid (2.00 g, 14.4 mmol) obtained in Step 1 was dissolved in DMF (29 mL), and potassium carbonate (7.95 g, 57.6 mmol) and benzyl bromide (5.13 mL, 43.2 mmol) were added thereto, followed by stirring at 50° C. for 2 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=2:1) to afford benzyl 1-benzyl-2-oxo-1,2-dihydropyridine-4-carboxylate (1.58 g, 34%) as a white solid.

Workup

extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with a saturated aqueous solution of sodium chloride
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was distilled away under reduced pressure
customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record: ord-9131dae1c97f4adc887d320fabeca988
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07880013B2

Reaction notes

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