Hydrochloric Acid → 1-(3-Amino-4,6-difluorophenyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1415949Notes

Reaction equation

HRID 1415949 reaction equation
[Cl:1][C:2]1[C:3]([F:30])=[C:4]([F:29])[CH:5]=[C:6]2[C:11]=1[N:10]([C:12]1[CH:17]=[C:16]([NH:18]C=O)[C:15]([F:21])=[CH:14][C:13]=1[F:22])[CH:9]=[C:8]([C:23]([O:25]CC)=[O:24])[C:7]2=[O:28].Cl>C(O)(=O)C>[NH2:18][C:16]1[CH:17]=[C:12]([N:10]2[C:11]3[C:6](=[CH:5][C:4]([F:29])=[C:3]([F:30])[C:2]=3[Cl:1])[C:7](=[O:28])[C:8]([C:23]([OH:25])=[O:24])=[CH:9]2)[C:13]([F:22])=[CH:14][C:15]=1[F:21]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54054955Ethyl 8-chloro-6,7-difluoro-1-(2,4-difluoro-5-formylaminophenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 108619991-(3-Amino-4,6-difluorophenyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 89.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 8-chloro-6,7-difluoro-1-(2,4-difluoro-5-formylaminophenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate (1.8 g) was added to 5 ml of hydrochloric acid and 20 ml of acetic acid. The solution was heated at reflux for 3 hours. The reaction solution was allowed to cool down and concentrated in vacua, and ethanol was added to the residue. The solid was collected by filtration and washed with diethyl ether to give 1.4 g of the title compound.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 3 hours
  3. temperatureto cool down
  4. concentrationconcentrated in vacua, and ethanol
  5. additionwas added to the residue
  6. filtrationThe solid was collected by filtration
  7. washwashed with diethyl ether

Sources & evidence

ORD record
ord-a6b8fa89e62e479ab0e6cce07a962b3b
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Reaction notes

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