Quinoline → 5-(Pyrimidin-4-yl)pyridin-2(1H)-one

HRID 1981294Notes

Reaction equation

HRID 1981294 reaction equation
[O:1]=[C:2]1[N:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][N:12]=2)=[CH:7][CH:3]1C(O)=O.N1C2C(=CC=CC=2)C=CC=1>CCOCC>[N:14]1[CH:15]=[CH:16][C:11]([C:8]2[CH:7]=[CH:3][C:2](=[O:1])[NH:10][CH:9]=2)=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 7047QuinolineHCID 70488940HCID 70488940, compound

Product 1

HCID 132766775-(Pyrimidin-4-yl)pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

90.8 g of 2-oxo-5-(4-pyrimidinyl)nicotinic acid was mixed with 900 ml of quinoline and then heated to reflux overnight. The mixture was then cooled and poured into 1800 ml of anhydrous ether. The mixture was stirred for 30 minutes, filtered and the solid was washed with 2 liters of ether. The solid was dried, recrystallized in 100 ml of hot dimethylformamide and dried to yield 5-(4-pyrimidyl)-2(1H)pyridone m.p. 250° C.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. temperatureThe mixture was then cooled
  4. filtrationfiltered
  5. washthe solid was washed with 2 liters of ether
  6. customThe solid was dried
  7. customrecrystallized in 100 ml of hot dimethylformamide
  8. customdried

Sources & evidence

ORD record
ord-81be085977bc4b6a9d08a9d6ccc72148
Source dataset
uspto-grants-1985_04
Patent number
US04514400

Reaction notes

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