Hydrochloric Acid → HCID 13960233, compound

HRID 2413967Notes

Reaction equation

HRID 2413967 reaction equation
C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2=[CH:17][C:18]([F:27])=[C:19]([N:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)[C:12]3=[C:13]2[N:8]([CH:9]([CH3:28])[CH:10]=[CH:11]3)[CH:7]=1)=[O:5])C.[OH-].[Na+].Cl>>[F:27][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])[CH:10]=[CH:11][C:12]=3[C:19]=1[N:20]1[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54467882HCID 54467882, compound

Product 1

HCID 13960233HCID 13960233, compoundYield 60.4%

Procedure

To 3.85 g (0.01 mole) of 9-fluoro-5-methyl-8- (4-methyl-1-piperazinyl) -1-oxo-1H, 5H-benzo[ij]quinolizine-2-carboxylic acid ethyl ester was added 50 ml of a 1N aqueous solution of sodium hydroxide. This mixture was stirred at 20°-25° C. for 17 hours to hydrolyze the starting material. The resulting reaction solution was adjusted to pH 6-7 by the addition of 1N hydrochloric acid under cooling with ice. The adjusted solution was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography [using a chloroform-methanol mixture (with a volume ratio of 2:1) as the developing solvent]. The fraction containing the desired product was evaporated to dryness under reduced pressure and the resulting residue was recrystallized from ethanol to obtain 2.16 g (60.4% yield) of 9-fluoro-5-methyl-8-(4-methyl-1-piperazinyl) -1-oxo-1H, 5H-benzo[ij]quinolizine-2-carboxylic acid in the form of pale-yellow crystals. These crystals had a melting point of 190°-195° C. (dec.).

Workup

  1. customThe resulting reaction solution
  2. temperatureunder cooling with ice
  3. concentrationThe adjusted solution was concentrated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography [
  5. additionThe fraction containing the desired product
  6. customwas evaporated to dryness under reduced pressure
  7. customthe resulting residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-43fb6530a68c47b59f0d1ebf125f4965
Source dataset
uspto-grants-1988_01
Patent number
US04720495

Reaction notes

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