Hydrochloric Acid → 1-Cyclopropyl-6,7-difluoro-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 2271275Notes

Reaction equation

HRID 2271275 reaction equation
Cl.[CH:2]1([N:5]2[C:14]3[C:9](=[C:10]([CH3:17])[C:11]([F:16])=[C:12]([F:15])[CH:13]=3)[C:8](=[O:18])[C:7]([C:19]([O:21]CC)=[O:20])=[CH:6]2)[CH2:4][CH2:3]1>C(O)(=O)C>[CH:2]1([N:5]2[C:14]3[C:9](=[C:10]([CH3:17])[C:11]([F:16])=[C:12]([F:15])[CH:13]=3)[C:8](=[O:18])[C:7]([C:19]([OH:21])=[O:20])=[CH:6]2)[CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14651255Ethyl 1-cyclopropyl-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 146512541-Cyclopropyl-6,7-difluoro-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 92.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

20 ml of 90% acetic acid and 5 ml of concentrated hydrochloric acid were added to 1.9 g of ethyl 1-cyclopropyl-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate, followed by refluxing for 2 hours. After cooling, the crystals precipitated were collected by filtration and washed with water, followed by washing with ethanol and then with diethyl ether to give 1.6 g of 1-cyclopropyl-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid.

Workup

  1. temperatureby refluxing for 2 hours
  2. temperatureAfter cooling
  3. customthe crystals precipitated
  4. filtrationwere collected by filtration
  5. washwashed with water
  6. washby washing with ethanol

Sources & evidence

ORD record
ord-2cee772da0e14e5f9d812df6f503c4a7
Source dataset
uspto-grants-2001_12
Patent number
US06333431B1

Reaction notes

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