Pyridine → HCID 23284812, compound

HRID 369293Notes

Reaction equation

HRID 369293 reaction equation
[N:1]1C=CC=C[CH:2]=1.CN.[NH2:9][C:10]1[C:11]([F:36])=[CH:12][C:13]([F:35])=[C:14]([N:16]2[C:25]3[C:20](=[CH:21][C:22]([N+:28]([O-:30])=[O:29])=[C:23](F)[C:24]=3[CH3:26])[C:19](=[O:31])[C:18]([C:32]([OH:34])=[O:33])=[CH:17]2)[CH:15]=1>C(OCC)C>[NH2:9][C:10]1[C:11]([F:36])=[CH:12][C:13]([F:35])=[C:14]([N:16]2[C:25]3[C:20](=[CH:21][C:22]([N+:28]([O-:30])=[O:29])=[C:23]([NH:1][CH3:2])[C:24]=3[CH3:26])[C:19](=[O:31])[C:18]([C:32]([OH:34])=[O:33])=[CH:17]2)[CH:15]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6329MethylamineHCID 23284757HCID 23284757, compound

Product 1

HCID 23284812HCID 23284812, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
40 °C

Procedure

Pyridine (500 mg) and a 40% aqueous solution (300 mg) of methylamine were added to 1-(5-amino-2,4-difluorophenyl)-7-fluoro-8-methyl-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (220 mg), and the mixture was stirred for 3 hours at 40° C. and for 2 days at room temperature. Diethyl ether was added to the reaction mixture, followed by stirring. A supernatant liquid was removed, and acetic acid (3 drops) was added to the residue, followed by stirring. Solids deposited were recrystallized from ethanol and N,N-dimethylformamide to obtain the title compound (190 mg) as a reddish brown powder.

Workup

  1. stirringby stirring
  2. customA supernatant liquid was removed
  3. additionacetic acid (3 drops) was added to the residue
  4. stirringby stirring
  5. customSolids deposited were recrystallized from ethanol and N,N-dimethylformamide

Sources & evidence

ORD record
ord-84179a8a97de476bb0c06d666f1b5067
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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