Citric Acid → HCID 23284748, compound

HRID 369334Notes

Reaction equation

HRID 369334 reaction equation
[NH2:1][C:2]1[C:3]([F:27])=[CH:4][C:5]([F:26])=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([N+:19]([O-:21])=[O:20])=[C:15](F)[CH:16]=3)[C:11](=[O:22])[C:10]([C:23]([OH:25])=[O:24])=[CH:9]2)[CH:7]=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:33]>>[NH2:1][C:2]1[C:3]([F:27])=[CH:4][C:5]([F:26])=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([N+:19]([O-:21])=[O:20])=[C:15]([OH:33])[CH:16]=3)[C:11](=[O:22])[C:10]([C:23]([OH:25])=[O:24])=[CH:9]2)[CH:7]=1

Participants

4

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 23284690HCID 23284690, compound

Product 1

HCID 23284748HCID 23284748, compound

Conditions

Temperature
40 °C

Procedure

1-(5-Amino-2,4-difluorophenyl)-7-fluoro-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (60 mg) was added to a 5% aqueous solution (3 ml) of sodium hydroxide, and the mixture was stirred at 40° C. for 2 hours. The reaction mixture was acidified with a 3% aqueous solution of citric acid, and solids formed were collected by filtration. The solids were subjected to azeotropic distillation with ethanol and toluene. Hexane was added to the residue to conduct filtration, thereby obtaining the title compound (49 mg) as a yellow powder.

Workup

  1. customformed
  2. filtrationwere collected by filtration
  3. distillationThe solids were subjected to azeotropic distillation with ethanol and toluene
  4. additionHexane was added to the residue
  5. filtrationfiltration

Sources & evidence

ORD record
ord-31703df0bb88436a9a4708176c6fbb19
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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