Water → HCID 10093902, compound

HRID 1905431Notes

Reaction equation

HRID 1905431 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1)[N:8]1[CH:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[S:20][C:7]1=[C:6]([C:27]([O:29]CC)=[O:28])[C:5]2=[O:32].[OH-].[K+].C(O)(C)(C)C.O.O>C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17]1)[N:8]1[CH:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[S:20][C:7]1=[C:6]([C:27]([OH:29])=[O:28])[C:5]2=[O:32]

Participants

5

Reactant 3

HCID 962WaterHCID 10343900HCID 10343900, compoundHCID 86743190HCID 86743190, compound

Product 1

HCID 10093902HCID 10093902, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

Three grams of ethyl 6-fluoro-7-(4-methyl-1-piperazinyl)-4-oxo-1-phenyl-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate was suspended in 30 ml of mixed solution of 5% potassium hydroxide/tert-butanol-water (75:25) and the suspension was heated at 50° C. for 4 hours with stirring. To this was added 30 to 40 ml of water to prepare homogeneous solution. The solution was neutralized with acetic acid and extracted with chloroform to which small amount of methanol was added. The extract was dried, concentrated, and the resulting residue was recrystallized from ethanol to give desired product. Yield: 2.23 g. M.p. 216°-217° C. (decomp.).

Workup

  1. customto prepare homogeneous solution
  2. extractionextracted with chloroform to which small amount of methanol
  3. additionwas added
  4. customThe extract was dried
  5. concentrationconcentrated
  6. customthe resulting residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-6171b45b3fea41bcadfef1c2ae48901e
Source dataset
uspto-grants-1989_06
Patent number
US04843070

Reaction notes

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