Methylamine → HCID 69961311, compound

HRID 369269Notes

Reaction equation

HRID 369269 reaction equation
[Cl:1][C:2]1[C:3](F)=[C:4]([F:27])[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[N+:20]([O-:22])=[O:21])[CH:9]=[C:8]([C:23]([OH:25])=[O:24])[C:7]2=[O:26].[CH3:29][NH2:30]>>[CH3:9][NH2:10].[Cl:1][C:2]1[C:3]([NH:30][CH3:29])=[C:4]([F:27])[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[N+:20]([O-:22])=[O:21])[CH:9]=[C:8]([C:23]([OH:25])=[O:24])[C:7]2=[O:26]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 23284711HCID 23284711, compound

Product 1

HCID 69961311HCID 69961311, compoundYield 145.3%

Procedure

8-Chloro-6,7-difluoro-1-(4-fluoro-5-hydroxy-2-nitrophenyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (150 mg) was added to an aqueous solution (about 40%; 750 mg) of methylamine, and the mixture was stirred at room temperature for 6 hours. The reaction mixture was concentrated under reduced pressure. A process of adding ethanol (2 ml) to the residue and then concentrating the mixture under reduced pressure was conducted 3 times repeatedly. Isopropyl alcohol (1.5 ml) was added to the resultant residue. Deposits were collected by filtration and washed with isopropyl alcohol and diisopropyl ether in that order to obtain the title compound (120 mg) as a yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. concentrationA process of adding ethanol (2 ml) to the residue and then concentrating the mixture under reduced pressure
  3. additionIsopropyl alcohol (1.5 ml) was added to the resultant residue
  4. filtrationDeposits were collected by filtration
  5. washwashed with isopropyl alcohol and diisopropyl ether in that order

Sources & evidence

ORD record
ord-469cdb08424041e28c944958927f0117
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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