Hydrochloric Acid → 1-(4-Amino-5-fluoropyrimidine-2-yl)-8-chloro 6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 610205Notes

Reaction equation

HRID 610205 reaction equation
Cl.C([NH:6][C:7]1[C:12]([F:13])=[CH:11][N:10]=[C:9]([N:14]2[C:23]3[C:18](=[CH:19][C:20]([F:26])=[C:21]([F:25])[C:22]=3[Cl:24])[C:17](=[O:27])[C:16]([C:28]([O:30]CC)=[O:29])=[CH:15]2)[N:8]=1)(C)(C)C>C(O)(=O)C>[NH2:6][C:7]1[C:12]([F:13])=[CH:11][N:10]=[C:9]([N:14]2[C:23]3[C:18](=[CH:19][C:20]([F:26])=[C:21]([F:25])[C:22]=3[Cl:24])[C:17](=[O:27])[C:16]([C:28]([OH:30])=[O:29])=[CH:15]2)[N:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22121180Ethyl 1-[4-(t-butylamino)-5-fluoropyrimidin-2-yl]-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 221211951-(4-Amino-5-fluoropyrimidine-2-yl)-8-chloro 6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 65.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixed solution (1:1, v/v) of 0.4 ml of 4N hydrochloric acid and 1 ml of acetic acid was added 90 mg of ethyl 1-[4-(t-butylamino)-5-fluoropyrimidin-2-yl]-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate, and the mixture was heated under reflux with stirring for 3 and half hours and allowed to cool. The precipitate was collected by filtration, and washed with ethanol and diisopropylether successively to obtain 48 mg of the title compound as a colorless powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. temperatureto cool
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with ethanol and diisopropylether successively

Sources & evidence

ORD record
ord-82252445906448a4afdfa1d33afec3ef
Source dataset
uspto-grants-1999_12
Patent number
US05998436

Reaction notes

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