Triethylamine → 1-(5-Amino-2,4-difluorophenyl)-8-chloro-7-dimethylamino-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid Hydrochloride

HRID 369228Notes

Reaction equation

HRID 369228 reaction equation
[NH2:1][C:2]1[C:3]([F:26])=[CH:4][C:5]([F:25])=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15](F)[C:16]=3[Cl:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)[CH:7]=1.Cl.[CH3:28][NH:29][CH3:30].C(N(CC)CC)C>C(#N)C>[ClH:18].[NH2:1][C:2]1[C:3]([F:26])=[CH:4][C:5]([F:25])=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15]([N:29]([CH3:30])[CH3:28])[C:16]=3[Cl:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 108619991-(3-Amino-4,6-difluorophenyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 699592811-(5-Amino-2,4-difluorophenyl)-8-chloro-7-dimethylamino-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid HydrochlorideYield 120.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

1-(5-Amino-2,4-difluorophenyl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (100 mg), dimethylamine hydrochloride (94 mg) and triethylamine (140 mg) were added to acetonitrile (10 ml), and the mixture was heated and stirred overnight at 60° C. After the reaction mixture was allowed to cool, the solvent was distilled off under reduced pressure. Ethanol and concentrated hydrochloric acid were added to the residue, and the mixture was concentrated again under reduced pressure. Ethanol was added to the residue, and solids were collected by filtration. The solids were washed successively with ethanol and diethyl ether to obtain the title compound (70 mg) as a yellow powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto cool
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionEthanol and concentrated hydrochloric acid were added to the residue
  5. concentrationthe mixture was concentrated again under reduced pressure
  6. additionEthanol was added to the residue, and solids
  7. filtrationwere collected by filtration
  8. washThe solids were washed successively with ethanol and diethyl ether

Sources & evidence

ORD record
ord-09325b36faca4258832515663e5e8d6d
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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