Acetic Acid → Diethyl 4-oxo-4H-quinolizine-1,3-dicarboxylate

HRID 255593

Reaction equation

HRID 255593 reaction equation
[O-]CC.[Na+].[N:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C([O:19][CH:20]=[C:21]([C:27](OCC)=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23])C.C(O)(=O)C>C(O)C>[CH2:15]([O:14][C:12]([C:11]1[CH:27]=[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:20](=[O:19])[N:5]2[C:6]=1[CH:7]=[CH:8][CH:9]=[CH:10]2)=[O:13])[CH3:16]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6871Diethyl (ethoxymethylene)malonateHCID 75960Ethyl 2-pyridylacetateHCID 2723922Sodium ethoxide

Product 1

HCID 262620Diethyl 4-oxo-4H-quinolizine-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of sodium ethoxide (sodium, 151 mg) in ethanol (20 ml) was added ethyl pyrid-2-ylacetate (1 ml) at room temperature and the mixture was stirred for 1 hour at the same temperature. To the mixture was added diethyl ethoxymethylenemalonate (1.33 ml) at room temperature and the mixture was stirred at room temperature overnight. To the mixture was added acetic acid (0.75 ml) at room temperature and the precipitate was filtered and washed with water to give 1,3-diethoxycarbonyl-4H-quinolizin-4-one (896 mg).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. filtrationthe precipitate was filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-1f75550736664cc0bc9eca4bd6b837ec
Source dataset
uspto-grants-1987_10
Patent number
US04698349

Linked notes

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