Citric Acid → HCID 23284701, compound

HRID 369335Notes

Reaction equation

HRID 369335 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.C[O-].[Na+].C(O)(=O)C[C:33](CC(O)=O)(C(O)=O)[OH:34]>N1C=CC=CC=1>[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]([O:34][CH3:33])[CH:16]=3)[C:11](=[O:22])[C:10]([C:23]([OH:25])=[O:24])=[CH:9]2)[CH:7]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 10942334Sodium MethoxideHCID 23284690HCID 23284690, compound

Product 1

HCID 23284701HCID 23284701, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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 mixed liquid of a 28% sodium methoxide solution (135 mg) and pyridine (0.5 ml), 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 (20 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-cd2f5c2f4d1b497b9b83c0d1ae320064
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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