Methylamine → HCID 23284738, compound

HRID 369264Notes

Reaction equation

HRID 369264 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1F)[N:8]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[C:16]([OH:21])[CH:15]=1)[CH:7]=[C:6]([C:22]([OH:24])=[O:23])[C:5]2=[O:25].[CH3:26][NH2:27]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[NH:27][CH3:26])[N:8]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[C:16]([OH:21])[CH:15]=1)[CH:7]=[C:6]([C:22]([OH:24])=[O:23])[C:5]2=[O:25]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 23284734HCID 23284734, compound

Product 1

HCID 23284738HCID 23284738, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

6,7-Difluoro-1-(4-fluoro-3-hydroxyphenyl)-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (403 mg) and an aqueous solution (about 40%; 2.0 g) of methylamine were added to pyridine (2.0 g), and the mixture was stirred at 60° C. for 6 days. The reaction mixture was concentrated under reduced pressure. A process of adding ethanol (5 ml) to the residue and then concentrating the mixture under reduced pressure was conducted 3 times repeatedly. Ethanol (2 ml) was added to the resultant residue, and deposits were collected by filtration and washed with ethanol and diisopropyl ether in that order to obtain the title compound (311 mg) as a colorless powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. concentrationA process of adding ethanol (5 ml) to the residue and then concentrating the mixture under reduced pressure
  3. additionEthanol (2 ml) was added to the resultant residue, and deposits
  4. filtrationwere collected by filtration
  5. washwashed with ethanol and diisopropyl ether in that order

Sources & evidence

ORD record
ord-9f264bad32044a80a3bb60640070b585
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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