Pyridine → HCID 23284753, compound

HRID 369253Notes

Reaction equation

HRID 369253 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.[CH3:28][NH:29][NH2:30].N1C=CC=CC=1>O>[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]([N:29]([CH3:28])[NH2:30])[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 1049PyridineHCID 6061MethylhydrazineHCID 23284690HCID 23284690, compound

Product 1

HCID 23284753HCID 23284753, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 methylhydrazine (32 mg) and pyridine (0.5 ml), and the mixture was stirred at room temperature for 3 hours. Water (5 ml) was added. At this time, the pH of the reaction mixture was about 5. Solids formed were collected by filtration and subjected to azeotropic distillation with ethanol and toluene. Hexane was added to the resultant residue to conduct filtration, thereby obtaining the title compound (60 mg) as a brown powder.

Workup

  1. customSolids formed
  2. filtrationwere collected by filtration
  3. distillationsubjected to azeotropic distillation with ethanol and toluene
  4. additionHexane was added to the resultant residue
  5. filtrationfiltration

Sources & evidence

ORD record
ord-eeb6f6d67aa5491e9e3330b2ae047852
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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