Methylamine → HCID 23284821, compound

HRID 369255Notes

Reaction equation

HRID 369255 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]=[C:16]([OH:18])[C:15]([F:19])=[CH:14][C:13]=1[F:20])[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]=[C:16]([OH:18])[C:15]([F:19])=[CH:14][C:13]=1[F:20])[CH:9]=[C:8]([C:21]([OH:23])=[O:22])[C:7]2=[O:24]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 23284761HCID 23284761, compound

Product 1

HCID 23284821HCID 23284821, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

8-Chloro-6,7-difluoro-1-(2,4-difluoro-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (200 mg) and an aqueous solution (about 40%; 550 mg) of methylamine were added to pyridine (1,200 mg), and the mixture was stirred at room temperature for 21 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 (173 mg) as a pale brown 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-61248dc4d86e43f9a0ac668a9c094461
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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