Pyridine → HCID 23284796, compound

HRID 369295Notes

Reaction equation

HRID 369295 reaction equation
[N:1]1C=CC=[CH:3][CH:2]=1.C(N)C.[NH2:10][C:11]1[C:12]([F:37])=[CH:13][C:14]([F:36])=[C:15]([N:17]2[C:26]3[C:21](=[CH:22][C:23]([N+:29]([O-:31])=[O:30])=[C:24](F)[C:25]=3[CH3:27])[C:20](=[O:32])[C:19]([C:33]([OH:35])=[O:34])=[CH:18]2)[CH:16]=1>C(OCC)C>[NH2:10][C:11]1[C:12]([F:37])=[CH:13][C:14]([F:36])=[C:15]([N:17]2[C:26]3[C:21](=[CH:22][C:23]([N+:29]([O-:31])=[O:30])=[C:24]([NH:1][CH2:2][CH3:3])[C:25]=3[CH3:27])[C:20](=[O:32])[C:19]([C:33]([OH:35])=[O:34])=[CH:18]2)[CH:16]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6341EthylamineHCID 23284757HCID 23284757, compound

Product 1

HCID 23284796HCID 23284796, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

Pyridine (300 mg) and a 70% aqueous solution (150 mg) of ethylamine were added to 1-(5-amino-2,4-difluorophenyl)-7-fluoro-8-methyl-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (110 mg), and the mixture was stirred at 50° C. for 3 hours. Diethyl ether was added to the reaction mixture, followed by stirring. A supernatant liquid was removed, and solids deposited were recrystallized from N,N-dimethylformamide. The solids were collected by filtration and washed with ethanol to obtain the title compound (75 mg) as a reddish brown powder.

Workup

  1. stirringby stirring
  2. customA supernatant liquid was removed
  3. customsolids deposited were recrystallized from N,N-dimethylformamide
  4. filtrationThe solids were collected by filtration
  5. washwashed with ethanol

Sources & evidence

ORD record
ord-3a22326eeced43d98da2fb88085b7742
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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