Methylamine → HCID 23284681, compound

HRID 369271Notes

Reaction equation

HRID 369271 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:10]1[C:19]2[C:14](=[CH:15][C:16]([F:22])=[C:17](F)[C:18]=2[CH3:20])[C:13](=[O:23])[C:12]([C:24]([OH:26])=[O:25])=[CH:11]1.[CH3:27][NH2:28]>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:10]1[C:19]2[C:14](=[CH:15][C:16]([F:22])=[C:17]([NH:28][CH3:27])[C:18]=2[CH3:20])[C:13](=[O:23])[C:12]([C:24]([OH:26])=[O:25])=[CH:11]1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 23284706HCID 23284706, compound

Product 1

HCID 23284681HCID 23284681, compoundYield 95.5%

Procedure

1-(2,4-Difluoro-5-hydroxyphenyl)-6,7-difluoro-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (300 mg) was added to an aqueous solution (about 40%; 3.0 g) of methylamine to conduct a reaction at 75° C. for 4 days. The reaction mixture was concentrated under reduced pressure. A process of adding ethanol (4 ml) to the residue and then concentrating the mixture under reduced pressure was conducted twice repeatedly. Ethanol (2 ml) was added to the resultant residue. Deposits were collected by filtration and washed with ethanol and diisopropyl ether in that order to obtain the title compound (295 mg) as a pale yellow powder.

Workup

  1. customa reaction at 75° C. for 4 days
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. concentrationA process of adding ethanol (4 ml) to the residue and then concentrating the mixture under reduced pressure
  4. additionEthanol (2 ml) was added to the resultant residue
  5. filtrationDeposits were collected by filtration
  6. washwashed with ethanol and diisopropyl ether in that order

Sources & evidence

ORD record
ord-32f24c0e036c4214aa5503a4674946c4
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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