Acetic Acid → 1-Cyclopropyl-6,7-difluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 330085Notes

Reaction equation

HRID 330085 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([F:15])[C:12]=3[CH3:14])[C:7](=[O:17])[C:6]([C:18]([O:20]CC)=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.S(=O)(=O)(O)O.C(O)(=O)C>O>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([F:15])[C:12]=3[CH3:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 9839540Ethyl 1-cyclopropyl-6,7-difluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 140525751-Cyclopropyl-6,7-difluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 88.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methyl-4-oxo-3-quinolinecarboxylate (1.97 g), concentrated sulfuric acid (1.6 ml) and acetic acid (12.8 ml) in water (9.6 ml) was refluxed for 1.5 hours. The reacting mixture was poured into ice-water (100 ml), the resulting precipitate was collected by filtration, washed with water and dried to give the title compound (1.58 g) as white powder, mp 243°-245° C.

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-c277c54610734964b827fdd9dc4f4835
Source dataset
uspto-grants-1990_01
Patent number
US04894458

Reaction notes

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