Benzoyl chloride → 4-Acetoxy-2-benzoyloxypyridine

HRID 466162Notes

Reaction equation

HRID 466162 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][NH:8][C:7](=[O:11])[CH:6]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCOCC1>[C:1]([O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([O:11][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 131631124-Acetoxy-2-pyridone

Product 1

HCID 140496164-Acetoxy-2-benzoyloxypyridineYield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 0.77 g quantity of 4-acetoxy-2-pyridone was suspended in 30 ml of dioxane. To the suspension were added 2.09 ml of triethylamine and 0.58 ml of benzoyl chloride and the mixture was stirred at room temperature for 2.5 hours. The reaction mixture was concentrated under reduced pressure and the residue was subjected to silica gel chromatography using, as an eluent, chloroform, giving 0.95 g of the title compound in a yield of 73%.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3ec8aad344994bd3ab0d1565b195d342
Source dataset
uspto-grants-1992_10
Patent number
US05155113

Reaction notes

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