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

HRID 1382745Notes

Reaction equation

HRID 1382745 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-406dcbe80eca4fccb82d2289879ae78f
Source dataset
uspto-grants-1989_02
Patent number
US04808584

Reaction notes

Loading…