Acetic Acid → HCID 14620490, compound

HRID 373516Notes

Reaction equation

HRID 373516 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([F:16])[C:10]([F:15])=[C:11]([F:14])[CH:12]=3)[C:7](=[O:17])[C:6]([C:18]([O:20]CC)=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.C(O)(=O)C.S(=O)(=O)(O)O>O>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([F:16])[C:10]([F:15])=[C:11]([F:14])[CH:12]=3)[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 14880201Ethyl 1-cyclopropyl-5,6,7-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 14620490HCID 14620490, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1.54 g of ethyl 1-cyclopropyl-5,6,7-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate, 8 ml of glacial acetic acid, 6 ml of water and 1 ml of conc. sulfuric acid was stirred at 120° C. for 1.5 hours. After cooling, the crystals which precipitated were collected by filtration, and washed successively with water and ethanol to give 1.34 g of 1-cyclopropyl-5,6,7-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid as colorless needles. m.p. 295°-297° C. (decomp.)

Workup

  1. temperatureAfter cooling
  2. customthe crystals which precipitated
  3. filtrationwere collected by filtration
  4. washwashed successively with water and ethanol

Sources & evidence

ORD record
ord-335dd18bc7eb457cb682de00031d23b2
Source dataset
uspto-grants-1992_11
Patent number
US05164392

Reaction notes

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