Ammonia → HCID 23284700, compound

HRID 369294Notes

Reaction equation

HRID 369294 reaction equation
[N:1]1C=CC=CC=1.N.[NH2:8][C:9]1[C:10]([F:35])=[CH:11][C:12]([F:34])=[C:13]([N:15]2[C:24]3[C:19](=[CH:20][C:21]([N+:27]([O-:29])=[O:28])=[C:22](F)[C:23]=3[CH3:25])[C:18](=[O:30])[C:17]([C:31]([OH:33])=[O:32])=[CH:16]2)[CH:14]=1>C(OCC)C>[NH2:1][C:22]1[C:23]([CH3:25])=[C:24]2[C:19]([C:18](=[O:30])[C:17]([C:31]([OH:33])=[O:32])=[CH:16][N:15]2[C:13]2[CH:14]=[C:9]([NH2:8])[C:10]([F:35])=[CH:11][C:12]=2[F:34])=[CH:20][C:21]=1[N+:27]([O-:29])=[O:28]

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 1049PyridineHCID 23284757HCID 23284757, compound

Product 1

HCID 23284700HCID 23284700, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

Pyridine (1.0 ml) and 28% aqueous ammonia (100 mg) were added to 1-(5-amino-2,4-difluorophenyl)-7-fluoro-8-methyl-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (100 mg), and the mixture was stirred at 50° C. for 2 days. Additional 28% aqueous ammonia (0.5 ml) was added, and the mixture was further stirred overnight at 50° C. Diethyl ether was added to the reaction mixture, followed by stirring. A supernatant liquid was removed, and ethanol was added to the residue. Solids deposited were collected by filtration and washed with ethanol to obtain the title compound (59 mg) as a yellow powder.

Workup

  1. waitthe mixture was further stirred overnight at 50° C
  2. stirringby stirring
  3. customA supernatant liquid was removed
  4. additionethanol was added to the residue
  5. filtrationSolids deposited were collected by filtration
  6. washwashed with ethanol

Sources & evidence

ORD record
ord-b1692de4cdcf4b8d9fae5f6c8ddc5f26
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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