Hydrochloric Acid → HCID 13960246, compound

HRID 2413968Notes

Reaction equation

HRID 2413968 reaction equation
C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2=[CH:17][C:18]([Cl:27])=[C:19]([N:20]3[CH2:25][CH2:24][NH:23][CH:22]([CH3:26])[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>C(O)C>[Cl: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[CH2:25][CH2:24][NH:23][CH:22]([CH3:26])[CH2:21]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53999312HCID 53999312, compound

Product 1

HCID 13960246HCID 13960246, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 4.02 g (0.01 mole) of 9-chloro-5-methyl-8-(3-methyl-1-piperazinyl)-1-oxo-1H, 5H-benzo[ij]quinolizine-2-carboxylic acid ethyl ester was added 120 ml of a mixture of 1N aqueous sodium hydroxide and ethanol (with a volume ratio of 5:1). This mixture was stirred at 20°-25° C. for 2 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. This solution was concentrated under reduced pressure, 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], and the fraction containing the desired product was collected. This fraction was evaporated to dryness under reduced pressure and the resulting residue was recrystallized from ethanol to obtain 2.89 g (77.3% yield) of 9-chloro-5-methyl-8-(3-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 200°-205° C. (dec.).

Workup

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

Sources & evidence

ORD record
ord-a894e09bea754e808c5f4b0fab914d59
Source dataset
uspto-grants-1988_01
Patent number
US04720495

Reaction notes

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