Hydrochloric Acid → 1-(3-Amino-4,6-difluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1415928Notes

Reaction equation

HRID 1415928 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:10]2[C:19]3[C:14](=[CH:15][C:16]([F:21])=[C:17]([F:20])[CH:18]=3)[C:13](=[O:22])[C:12]([C:23]([O:25]CC)=[O:24])=[CH:11]2)[C:5]([F:9])=[CH:6][C:7]=1[F:8].Cl>C(O)(=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([N:10]2[C:19]3[C:14](=[CH:15][C:16]([F:21])=[C:17]([F:20])[CH:18]=3)[C:13](=[O:22])[C:12]([C:23]([OH:25])=[O:24])=[CH:11]2)[C:5]([F:9])=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54141710Ethyl 1-(3-amino-4,6-difluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 109481431-(3-Amino-4,6-difluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 89.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 1-(3-amino-4,6-difluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (1 g) was added to 8 ml of acetic acid and 2 ml of hydrochloric acid. The solution was heated at reflux overnight. After cooling down, the solution was concentrated in vacua. Ethanol was added to the residue whereupon the solid was collected by filtration and washed with diethyl ether to give 830 mg of the title compound.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling down
  4. concentrationthe solution was concentrated in vacua
  5. additionEthanol was added to the residue whereupon the solid
  6. filtrationwas collected by filtration
  7. washwashed with diethyl ether

Sources & evidence

ORD record
ord-c61714ffc91740c9a679ec16912e4c54
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Reaction notes

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