Pyridine → HCID 19815234, compound

HRID 466144Notes

Reaction equation

HRID 466144 reaction equation
[Cl:1][C:2]1[C:3]([O:9][C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[N:13][CH:12]=2)=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.O1CCOCC1.N1C=CC=CC=1.[C:30](Cl)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(N(CC)CC)C>[C:30]([O:8][C:5]1[CH:4]=[C:3]([O:9][C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[N:13][CH:12]=2)[C:2]([Cl:1])=[CH:7][N:6]=1)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 312751,4-DioxaneHCID 14049649HCID 14049649, compound

Product 1

HCID 19815234HCID 19815234, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A 300 ml quantity of 5-chloro-4-nicotinoyloxy-2-pyridone was suspended in a mixture solvent of 30 ml of dioxane and 10 ml of pyridine and to the suspension were added 0.17 ml of benzoyl chloride and 0.83 ml of triethylamine. The mixture was refluxed for 3 hours. The resulting reaction mixture was concentrated and the concentrate was subjected to silica gel column chromatography using as an eluent, chloroform, thereby producing 230 mg of the title compound in a yield of 54%.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. customThe resulting reaction mixture
  3. concentrationwas concentrated

Sources & evidence

ORD record
ord-411fd2b71e96474792cf3dd38ce28608
Source dataset
uspto-grants-1992_10
Patent number
US05155113

Reaction notes

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