Sulfuric Acid → ethyl 7,8,9-trifluoro-1-hydroxymethyl-5-oxo-5H-thiazolo[3,2-a]quinoline-4-carboxylate

HRID 1722074Notes

Reaction equation

HRID 1722074 reaction equation
C([O:4][CH2:5][C:6](=O)[CH2:7][S:8][C:9]1[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:17]([OH:24])[C:16]2[C:11](=[C:12]([F:27])[C:13]([F:26])=[C:14]([F:25])[CH:15]=2)[N:10]=1)(=O)C.S(=O)(=O)(O)O>O>[F:25][C:14]1[CH:15]=[C:16]2[C:11](=[C:12]([F:27])[C:13]=1[F:26])[N:10]1[C:6]([CH2:5][OH:4])=[CH:7][S:8][C:9]1=[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:17]2=[O:24]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 178470106HCID 178470106, compound

Product 1

HCID 14673307ethyl 7,8,9-trifluoro-1-hydroxymethyl-5-oxo-5H-thiazolo[3,2-a]quinoline-4-carboxylateYield 78.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 2-(3-acetoxy-2-oxopropylthio)-6,7,8-trifluoro-4-hydroxyquinoline-3-carboxylate (3.54 g) was added to concd. sulfuric acid (35 ml) and the mixture was stirred at room temperature for 2 hours and 15 minutes. Thereto water (29 ml) was added gradually with ice-cooling and the mixture was stirred at room temperature for 26 hours, followed by addition of ice-water (400 ml). After precipitated crystal was filtered and washed with water, the resultant was recrystallized from a mixed solvent of chloroform-ethanol to give the title compound (2.38 g) as pale yellow crystals.

Workup

  1. temperaturecooling
  2. customAfter precipitated crystal
  3. filtrationwas filtered
  4. washwashed with water
  5. customthe resultant was recrystallized from a mixed solvent of chloroform-ethanol

Sources & evidence

ORD record
ord-c0815552961e4b77bb0bd3aaf441ca60
Source dataset
uspto-grants-1989_08
Patent number
US04853469

Reaction notes

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