Ethyl 1-cyclopropyl-6,7,8-trifluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate → 1-Cyclopropyl-5-methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 2073818Notes

Reaction equation

HRID 2073818 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:17])[C:10]([F:16])=[C:11]([F:15])[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([O:21]CC)=[O:20])=[CH:5]2)[CH2:3][CH2:2]1>Cl>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:17])[C:10]([F:16])=[C:11]([F:15])[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:2][CH2:3]1

Participants

3

Reactant 1

HCID 14651259Ethyl 1-cyclopropyl-6,7,8-trifluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 146512581-Cyclopropyl-5-methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 93.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 4.6 g (14.1 mmol) of ethyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylate in 100 ml of 6M hydrochloric acid was refluxed for four hours. The solution was cooled to room temperature and the solids were filtered, washed with water, and dried to give 3.9 g of the title compound, mp 234°-235° C.

Workup

  1. temperaturewas refluxed for four hours
  2. filtrationthe solids were filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-cac5285d37ee478a80ef6d783b37cb39
Source dataset
uspto-grants-1990_04
Patent number
US04920120

Reaction notes

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