Triethylamine → 6-Benzoyloxy-2-(4-bromobenzoyloxy)-3-cyanopyridine

HRID 466163Notes

Reaction equation

HRID 466163 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1.[C:18]([O:26][C:27]1[N:32]=[C:31]([OH:33])[C:30]([C:34]#[N:35])=[CH:29][CH:28]=1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCOCC1>[C:18]([O:26][C:27]1[N:32]=[C:31]([O:33][C:13](=[O:14])[C:12]2[CH:16]=[CH:17][C:9]([Br:8])=[CH:10][CH:11]=2)[C:30]([C:34]#[N:35])=[CH:29][CH:28]=1)(=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 685154-Bromobenzoyl chlorideHCID 178510098HCID 178510098, compound

Product 1

HCID 140496396-Benzoyloxy-2-(4-bromobenzoyloxy)-3-cyanopyridineYield 84.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Triethylamine (3.46 ml) and 1.82 g of 4-bromobenzoyl chloride were added to a solution of 2.00 g of 6-benzoyloxy-3-cyano-2-hydroxypyridine in 50 ml of dioxane. The mixture was stirred at room temperature for 1 hour. The salt thus produced was separated by filtration and the filtrate was concentrated. The concentrate was applied to silica gel column chromatography using, as an eluent, chloroform, giving 2.97 g of the title compound in a yield of 84%.

Workup

  1. customThe salt thus produced
  2. customwas separated by filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1e9698ab616546c7bf5277b6b970ac44
Source dataset
uspto-grants-1992_10
Patent number
US05155113

Reaction notes

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