Acetic Anhydride → HCID 20133482, compound

HRID 845031Notes

Reaction equation

HRID 845031 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:19])[C:11]=1[N:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1)[N:8]([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)[CH:7]=[C:6]([C:27]([OH:29])=[O:28])[C:5]2=[O:30].[C:31](OC(=O)C)(=[O:33])[CH3:32]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:19])[C:11]=1[N:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1)[N:8]([C:20]1[CH:21]=[CH:22][C:23]([O:26][C:31](=[O:33])[CH3:32])=[CH:24][CH:25]=1)[CH:7]=[C:6]([C:27]([OH:29])=[O:28])[C:5]2=[O:30]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 20133480HCID 20133480, compound

Product 1

HCID 20133482HCID 20133482, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

6,8-Difluoro-7-(4-methyl-1-piperazinyl)-1-(4-hydroxyphenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.14 g) is dissolved in dry pyridine (5 ml) and acetic anhydride (5 ml), and the mixture is allowed to stand at room temperature for 16 hours. Excess acetic anhydride and pyridine are distilled off under reduced pressure, and the resulting residue is dissolved in dichloromethane. The dichloromethane solution is washed with diluted hydrochloric acid, saturated aqueous sodium chloride, saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride in this order, and dried over sodium sulfate. The solvent is distilled off, and the residue is recrystallized from ethanol-chloroform to give 6,8-difluoro-7-(4-methyl-1-piperazinyl)-1-(4-acetyloxyphenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.12 g) as pale yellowish white crystals, m.p. 247°-251° C.

Workup

  1. distillationExcess acetic anhydride and pyridine are distilled off under reduced pressure
  2. dissolutionthe resulting residue is dissolved in dichloromethane
  3. washThe dichloromethane solution is washed with diluted hydrochloric acid, saturated aqueous sodium chloride, saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride in this order
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent is distilled off
  6. customthe residue is recrystallized from ethanol-chloroform

Sources & evidence

ORD record
ord-c6299ec62c9c4ef7a0f3b99b1441963c
Source dataset
uspto-grants-1988_07
Patent number
US04755513

Reaction notes

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