Acetic Acid → 5-Benzylamino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 2050627Notes

Reaction equation

HRID 2050627 reaction equation
S(=O)(=O)(O)O.C(O)(=O)C.C([N:13]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:14]1[C:23]([F:24])=[C:22]([F:25])[CH:21]=[C:20]2[C:15]=1[C:16](=[O:34])[C:17]([C:29]([O:31]CC)=[O:30])=[CH:18][N:19]2[CH:26]1[CH2:28][CH2:27]1)(=O)C>O>[CH2:35]([NH:13][C:14]1[C:23]([F:24])=[C:22]([F:25])[CH:21]=[C:20]2[C:15]=1[C:16](=[O:34])[C:17]([C:29]([OH:31])=[O:30])=[CH:18][N:19]2[CH:26]1[CH2:27][CH2:28]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 14880248ethyl 5-(N-acetylbenzylamino)-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 148802085-Benzylamino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 81.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Twenty milliliters of a mixture of conc. sulfuric acid, glacial acetic acid and water (1:8:6) was added to 4.4 g of ethyl 5-(N-acetylbenzylamino)-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate, and the mixture was heated under reflux for 6 hours. After cooling, water was added to the reaction mixture, and the crystals were collected by filtration and successively washed with water and ethanol. The crystals were recrystallized from chloroform/ethanol to give 3.0 g of 5-benzylamino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. m.p. 214°-216° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hours
  3. temperatureAfter cooling
  4. filtrationthe crystals were collected by filtration
  5. washsuccessively washed with water and ethanol
  6. customThe crystals were recrystallized from chloroform/ethanol

Sources & evidence

ORD record
ord-9168a920d61a48efbd9f0ccf743620be
Source dataset
uspto-grants-1991_05
Patent number
US05013841

Reaction notes

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