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

HRID 1906206Notes

Reaction equation

HRID 1906206 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).

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-d477bd4169604fa886ebe36528287943
Source dataset
uspto-grants-1987_03
Patent number
US04650804

Reaction notes

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