Methylamine → HCID 23284717, compound

HRID 369260Notes

Reaction equation

HRID 369260 reaction equation
[Cl:1][C:2]1[C:3](F)=[C:4]([F:25])[CH:5]=[C:6]2[C:11]=1[N:10]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[C:14]([O:19][CH3:20])[CH:13]=1)[CH:9]=[C:8]([C:21]([OH:23])=[O:22])[C:7]2=[O:24].[CH3:27][NH2:28]>N1C=CC=CC=1>[Cl:1][C:2]1[C:3]([NH:28][CH3:27])=[C:4]([F:25])[CH:5]=[C:6]2[C:11]=1[N:10]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[C:14]([O:19][CH3:20])[CH:13]=1)[CH:9]=[C:8]([C:21]([OH:23])=[O:22])[C:7]2=[O:24]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 23284724HCID 23284724, compound

Product 1

HCID 23284717HCID 23284717, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

8-Chloro-6,7-difluoro-1-(4-fluoro-3-methoxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (160 mg) and an aqueous solution (about 40%; 400 mg) of methylamine were added to pyridine (1,000 mg), and the mixture was stirred at room temperature for 27 hours. The reaction mixture was concentrated under reduced pressure, and ethanol (1 ml) was added to the residue. Deposits were collected by filtration and washed with ethanol and diisopropyl ether in that order to obtain the title compound (145 mg) as a colorless powder

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and ethanol (1 ml)
  2. additionwas added to the residue
  3. filtrationDeposits were collected by filtration
  4. washwashed with ethanol and diisopropyl ether in that order

Sources & evidence

ORD record
ord-2f8dce45b939435e85fcbf52ed64beac
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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