Water → 1-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1762743Notes

Reaction equation

HRID 1762743 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11]([F:14])[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([O:19]CC)=[O:18])=[CH:5]2)[CH2:3][CH2:2]1.O.S(=O)(=O)(O)O>C(O)(=O)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11]([F:14])[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 9817544Ethyl 1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 52104221-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 81.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 6,8 g of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, ethyl ester in a mixture of 46 ml of glacial acetic acid, 35 ml of water and 4.5 ml of concentrated sulfuric acid was refluxed for 1.5 hours. The resulting suspension was cooled in an ice bath, the solid collected, washed with cold water, dried and recrystallized from hot dimethylformamide, giving 5 g of the desired compound, mp 288°-290° C.

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. temperatureThe resulting suspension was cooled in an ice bath
  3. customthe solid collected
  4. washwashed with cold water
  5. customdried
  6. customrecrystallized from hot dimethylformamide

Sources & evidence

ORD record
ord-e4fa46ccf0574741bf7ddf88def2e16e
Source dataset
uspto-grants-1989_05
Patent number
US04833270

Reaction notes

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