Hydrochloric Acid → 4H-Quinolizine-3-carboxylic acid, 7-butoxy-4-oxo-1-phenyl-, ethyl ester

HRID 255592Notes

Reaction equation

HRID 255592 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[N:14]2[C:9]([CH:10]=[CH:11][C:12]([OH:17])=[CH:13]2)=[C:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:7]=1)=[O:5])[CH3:2].[H-].[Na+].[CH2:26](I)[CH2:27][CH2:28][CH3:29].Cl>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[N:14]2[C:9]([CH:10]=[CH:11][C:12]([O:17][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:13]2)=[C:8]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 201836663-ethoxycarbonyl-7-hydroxy-1-phenyl-4H-quinolizin-4-one

Product 1

HCID 156320784H-Quinolizine-3-carboxylic acid, 7-butoxy-4-oxo-1-phenyl-, ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-ethoxycarbonyl-7-hydroxy-1-phenyl-4H-quinolizin-4-one (5 g) in N,N-dimethylformamide (100 ml) was added sodium hydride (63.6% in mineral oil, 732 mg) at 50° C. After stirring for 30 minutes at 50° C., n-butyliodide (2.77 ml) was added. After stirring for 1 hour at 50° C., the mixture was cooled to room temperature and added to a mixture of aqueous hydrogen chloride and an ice. The mixture was extracted with chloroform and the chloroform extract was washed with 10% aqueous sodium hydrogen carbonate and aqueous saturated sodium chloride. After drying over magnesium sulfate, the chloroform extract was filtered and concentrated in vacuo. The residue was chromatographed on silica gel (Merck 70-230 mesh, 100 g), eluting with chloroform and then 10% methanol in chloroform to give 3-ethoxycarbonyl-7-(n-butoxy)-1-phenyl-4H-quinolizin-4-one (2.37 g).

Workup

  1. stirringAfter stirring for 1 hour at 50° C.
  2. temperaturethe mixture was cooled to room temperature
  3. extractionThe mixture was extracted with chloroform
  4. extractionthe chloroform extract
  5. washwas washed with 10% aqueous sodium hydrogen carbonate and aqueous saturated sodium chloride
  6. dry with materialAfter drying over magnesium sulfate
  7. extractionthe chloroform extract
  8. filtrationwas filtered
  9. concentrationconcentrated in vacuo
  10. customThe residue was chromatographed on silica gel (Merck 70-230 mesh, 100 g)
  11. washeluting with chloroform

Sources & evidence

ORD record
ord-305c9bdd819047a4b49f1b9cf547b0ed
Source dataset
uspto-grants-1987_10
Patent number
US04698349

Reaction notes

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