Ethanol → HCID 13116419, compound

HRID 2295721Notes

Reaction equation

HRID 2295721 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:21])[C:7]([C:16]([O:18]CC)=[O:17])=[C:8]3[S:14][CH2:13][CH:12]([CH3:15])[N:9]32)=[CH:4][C:3]=1[F:22].C(O)C.[OH-].[K+]>>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:21])[C:7]([C:16]([OH:18])=[O:17])=[C:8]3[S:14][CH2:13][CH:12]([CH3:15])[N:9]32)=[CH:4][C:3]=1[F:22]

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 13116417HCID 13116417, compound

Product 1

HCID 13116419HCID 13116419, compoundYield 93.7%

Procedure

Then 600 mg (1.55 mmol) of ethyl 8-bromo-7-fluoro-1-methyl-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a)quinoline-4-carboxylate separated by column chromatography was suspended in 50 ml of ethanol containing 1.2 grams (0.02 mol) of potassium hydroxide and the mixture was heated to reflux for 1.5 hours. The content was concentrated under reduced pressure and, after water was added to the residue, insoluble matters were filtered and removed. This was acidified with acetic acid and crystals separated therefrom were collected by filtration, washed with water and dried to give 520 mg (93.7 percent) of the title compound. Recrystallized from dimethyl formamide. Melting point 290° to 291° C. (decomposition). Elementary analysis calculated as C13H9BrFNO3S: C 43.59, H 2.53, N 3.91; Found: C 43.78, H 2.55, N 3.93.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1.5 hours
  3. concentrationThe content was concentrated under reduced pressure
  4. additionafter water was added to the residue, insoluble matters
  5. filtrationwere filtered
  6. customremoved
  7. customseparated
  8. filtrationtherefrom were collected by filtration
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-8676f71957554a5fbdfc818eb503a6ef
Source dataset
uspto-grants-1984_01
Patent number
US04426381

Reaction notes

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