4h-Quinolizin-4-one-3-carboxamide → 3-cyano-4H-quinolizin-4-one

HRID 255596Notes

Reaction equation

HRID 255596 reaction equation
[CH:1]1[CH:2]=[C:3]([C:12]([NH2:14])=O)[C:4](=[O:11])[N:5]2[C:10]=1[CH:9]=[CH:8][CH:7]=[CH:6]2>P(Cl)(Cl)(Cl)=O>[C:12]([C:3]1[C:4](=[O:11])[N:5]2[C:10]([CH:9]=[CH:8][CH:7]=[CH:6]2)=[CH:1][CH:2]=1)#[N:14]

Participants

3

Reactant 1

HCID 119605794h-Quinolizin-4-one-3-carboxamide

Product 1

HCID 156321213-cyano-4H-quinolizin-4-one

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture of 4H-quinolizin-4-one-3-carboxamide (1.0 g) and phosphorus oxychloride (50 ml) was refluxed for one hour. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in aqueous sodium bicarbonate solution and chloroform. The chloroform extract was washed with water, dried over anhydrous magnesium sulfate and then evaporated. The residue was chromatographed on silica gel (30 g) eluting with chloroform-methanol (50:1) to give 3-cyano-4H-quinolizin-4-one, which on recrystallization from ether gave crystals (800 mg), mp. 198°-200° C.

Workup

  1. temperaturewas refluxed for one hour
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in aqueous sodium bicarbonate solution
  4. extractionThe chloroform extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. customThe residue was chromatographed on silica gel (30 g)
  9. washeluting with chloroform-methanol (50:1)

Sources & evidence

ORD record
ord-67bc4b0134614ff5bc71142328fecad5
Source dataset
uspto-grants-1987_10
Patent number
US04698349

Reaction notes

Loading…