Ammonia → 4h-Quinolizin-4-one-3-carboxamide

HRID 255595Notes

Reaction equation

HRID 255595 reaction equation
[CH:1]1[CH:2]=[C:3]([C:12]([OH:14])=O)[C:4](=[O:11])[N:5]2[C:10]=1[CH:9]=[CH:8][CH:7]=[CH:6]2.C(N1C=CN=C1)([N:17]1C=CN=C1)=O.N>CN(C)C=O>[CH:1]1[CH:2]=[C:3]([C:12]([NH2:17])=[O:14])[C:4](=[O:11])[N:5]2[C:10]=1[CH:9]=[CH:8][CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 15632080HCID 15632080, compound

Product 1

HCID 119605794h-Quinolizin-4-one-3-carboxamideYield 85.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 4H-quinolizin-4-one-3-carboxylic acid (2.27 g) in dry N,N-dimethylformamide (22.7 ml) was added 1,1'-carbonyldiimidazole (2.92 g). The resulting suspension was heated to 100° C. and kept for 30 minutes. After cooling to room temperature the resulting solution was treated with dry ammonia and stirred for 20 minutes. The crystals separated was collected by filtration and washed with water to give 4H-quinolizin-4-one-3-carboxamide (1.94 g). mp. 230°-232° C.

Workup

  1. temperatureAfter cooling to room temperature the resulting solution
  2. customThe crystals separated
  3. filtrationwas collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-6af7c792e74041599dad84f7e718ff80
Source dataset
uspto-grants-1987_10
Patent number
US04698349

Reaction notes

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