Hydrochloric Acid → 4H-quinolizin-4-one-1,3-dicarboxylic acid

HRID 255600Notes

Reaction equation

HRID 255600 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:17]([O:19]CC)=[O:18])[C:9](=[O:16])[N:10]2[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]2)=[O:5])C.[OH-].[Na+].Cl>CO>[C:6]1([C:4]([OH:5])=[O:3])[CH:7]=[C:8]([C:17]([OH:19])=[O:18])[C:9](=[O:16])[N:10]2[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 262620Diethyl 4-oxo-4H-quinolizine-1,3-dicarboxylate

Product 1

HCID 139212454H-quinolizin-4-one-1,3-dicarboxylic acidYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1,3-diethoxycarbonyl-4H-quinolizin-4-one (896 mg) in methanol (9 ml) was added 6N aqueous sodium hydroxide (2.58 ml) at room temperature and the mixture was heated with reflux for an hour. After cooling to 0° C., the reaction mixture was acidified to pH 2 with 6N hydrochloric acid and the precipitate was filtered and washed with water to give 4H-quinolizin-4-one-1,3-dicarboxylic acid (202 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperaturewith reflux for an hour
  3. filtrationthe precipitate was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-93a652526910429c87415cb6447a0262
Source dataset
uspto-grants-1987_10
Patent number
US04698349

Reaction notes

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