Acetic Acid → HCID 13960207, compound

HRID 2413964Notes

Reaction equation

HRID 2413964 reaction equation
C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2=[CH:17][C:18]([F:26])=[C:19]([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[C:12]3=[C:13]2[N:8]([CH:9]([CH3:28])[CH2:10][C:11]3=[O:27])[CH:7]=1)=[O:5])C.[OH-].[Na+].C(O)(=O)C>C(O)C>[F:26][C:18]1[CH:17]=[C:14]2[C:13]3[N:8]([CH:7]=[C:6]([C:4]([OH:5])=[O:3])[C:15]2=[O:16])[CH:9]([CH3:28])[CH2:10][C:11](=[O:27])[C:12]=3[C:19]=1[N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 13960202HCID 13960202, compound

Product 1

HCID 13960207HCID 13960207, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.87 g (0.01 mole) of 9-fluoro-5-methyl-8-(1-piperazinyl)-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid ethyl ester was suspended in 12 ml of ethanol, 50 ml of a 2N aqueous solution of sodium hydroxide was added thereto, and this mixture was stirred at 20°-25° C. for 2 hours to hydrolyze the starting material. The resulting reaction solution was adjusted to pH 4-5 by the addition of acetic acid under cooling with ice. The precipitate which separated out was collected by filtration and recrystallized from ethanol to obtain 2.91 g (81.0% yield) of 9-fluoro-5-methyl-8-(1-piperazinyl)-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid in the form of yellow crystals. These crystals had a melting point of 261°-263° C. (dec.).

Workup

  1. customThe resulting reaction solution
  2. temperatureunder cooling with ice
  3. customThe precipitate which separated out
  4. filtrationwas collected by filtration
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-9999158176464418b649efd409c54e31
Source dataset
uspto-grants-1988_01
Patent number
US04720495

Reaction notes

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