Citric Acid → HCID 86700036, compound

HRID 1428086Notes

Reaction equation

HRID 1428086 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11](=[O:19])[C:12]([C:16]([OH:18])=[O:17])=[CH:13][NH:14][CH:15]=2)=[CH:6][CH:5]=1.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[CH2:20]([N:14]1[CH:15]=[C:10]([C:7]2[CH:6]=[CH:5][C:4]([F:3])=[CH:9][CH:8]=2)[C:11](=[O:19])[C:12]([C:16]([OH:18])=[O:17])=[CH:13]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 5

HCID 311Citric AcidHCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 602042075-(4-Fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid

Product 1

HCID 86700036HCID 86700036, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Fifty-five percent sodium hydride (131 mg) dispersed in oil was added to a solution of 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid (233 mg) in DMF (5 ml) under ice cooling, and the mixture was stirred at room temperature for one hour. Benzyl bromide (356 μl) was then added and the mixture was stirred for two days. A 1 N aqueous sodium hydroxide solution was then added, followed by stirring overnight. A 10% aqueous citric acid solution was added to the reaction solution, and the precipitate was collected by filtration to give the title compound (253 mg) as a solid.

Workup

  1. stirringthe mixture was stirred for two days
  2. stirringby stirring overnight
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-aefafab4835e486b91ac6c0845a5dbc0
Source dataset
uspto-grants-2015_01
Patent number
US08933103B2

Reaction notes

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