Ethanol → 8-bromo-7-fluoro-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a) quinoline-4-carboxylic acid

HRID 2295718Notes

Reaction equation

HRID 2295718 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:20])[C:7]([C:15]([O:17]CC)=[O:16])=[C:8]3[S:14][CH2:13][CH2:12][N:9]32)=[CH:4][C:3]=1[F:21].[OH-].[Na+].O.C(O)C>C(O)(=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:20])[C:7]([C:15]([OH:17])=[O:16])=[C:8]3[S:14][CH2:13][CH2:12][N:9]32)=[CH:4][C:3]=1[F:21]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 13116414ethyl 8-bromo-7-fluoro-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a)-quinoline-4-carboxylate

Product 1

HCID 131164168-bromo-7-fluoro-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a) quinoline-4-carboxylic acidYield 93.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Then 1.0 gram of the fractioned ethyl 8-bromo-7-fluoro-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a)-quinoline-4-carboxylate was suspended in a solution of 2.0 grams of sodium hydroxide (0.05 mmol), 50 ml of water and 20 ml of ethanol, the mixture was heated to reflux for four hours, the transparent solution was acidified with acetic acid after being cooled, crystals separated out were collected by filtration, washed with water, and dried. Thus, 860 mg (93.5 percent) of the title compound was obtained. Colorless powdery crystals were then recrystallized from dimethyl formamide. Melting point was 228° to 290° C. (decomposition).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for four hours
  3. temperatureafter being cooled
  4. customcrystals separated out
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-00639b1e67b94962ad2ea5bac2b77925
Source dataset
uspto-grants-1984_01
Patent number
US04426381

Reaction notes

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