Ammonia → HCID 23284818, compound

HRID 369252Notes

Reaction equation

HRID 369252 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.[NH3:28].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>N1C=CC=CC=1>[NH2:28][C:15]1[CH:16]=[C:17]2[C:12]([C:11](=[O:22])[C:10]([C:23]([OH:25])=[O:24])=[CH:9][N:8]2[C:6]2[CH:7]=[C:2]([NH2:1])[C:3]([F:27])=[CH:4][C:5]=2[F:26])=[CH:13][C:14]=1[N+:19]([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 311Citric AcidHCID 23284690HCID 23284690, compound

Product 1

HCID 23284818HCID 23284818, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

1-(5-Amino-2,4-difluorophenyl)-7-fluoro-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (70 mg) was added to a mixed liquid of 28% aqueous ammonia (85 mg) and pyridine (2 ml), and the mixture was stirred at 50° C. for 15 hours. The reaction mixture was acidified with 3% citric acid (20 ml), 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 obtain the title compound (50 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-982cd13b21fa42a98c74b35550d0af58
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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