Methylamine → HCID 23284823, compound

HRID 369262Notes

Reaction equation

HRID 369262 reaction equation
[Cl:1][C:2]1[C:3](F)=[C:4]([F:24])[CH:5]=[C:6]2[C:11]=1[N:10]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[C:14]([OH:19])[CH:13]=1)[CH:9]=[C:8]([C:20]([OH:22])=[O:21])[C:7]2=[O:23].[CH3:26][NH2:27]>N1C=CC=CC=1>[Cl:1][C:2]1[C:3]([NH:27][CH3:26])=[C:4]([F:24])[CH:5]=[C:6]2[C:11]=1[N:10]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[C:14]([OH:19])[CH:13]=1)[CH:9]=[C:8]([C:20]([OH:22])=[O:21])[C:7]2=[O:23]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 23284731HCID 23284731, compound

Product 1

HCID 23284823HCID 23284823, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

8-Chloro-6,7-difluoro-1-(4-fluoro-3-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (300 mg) and an aqueous solution (about 40%; 600 mg) of methylamine were added to pyridine (1,500 mg), and the mixture was stirred at room temperature for 63 hours. The reaction mixture was concentrated under reduced pressure. A process of adding ethanol (3 ml) to the residue and then concentrating the mixture under reduced pressure was conducted twice repeatedly. Ethanol (4 ml) was added to the resultant residue, and the mixture was heated under reflux for 30 minutes. The reaction mixture was allowed to cool, and deposits were collected by filtration and washed with ethanol and diisopropyl ether in that order to obtain the title compound (305 mg) as a colorless powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. concentrationA process of adding ethanol (3 ml) to the residue and then concentrating the mixture under reduced pressure
  3. additionEthanol (4 ml) was added to the resultant residue
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 30 minutes
  6. temperatureto cool
  7. filtrationdeposits were collected by filtration
  8. washwashed with ethanol and diisopropyl ether in that order

Sources & evidence

ORD record
ord-13ee304c002b4716863d12fc43439e79
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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