HCID 22388054, compound → HCID 86585540, compound

HRID 1072786Notes

Reaction equation

HRID 1072786 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]3[CH:20]=[C:19]([C:21]([OH:23])=[O:22])[CH:18]=[CH:17][N:16]=3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[CH2:29](O)[CH3:30]>>[C:1]1([C:7]2[CH:8]=[CH:9][C:10](/[CH:13]=[CH:14]/[C:15]3[CH:20]=[C:19]([C:21]([O:23][CH2:29][CH3:30])=[O:22])[CH:18]=[CH:17][N:16]=3)=[CH:11][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 22388054HCID 22388054, compoundHCID 73950302Sulphuric acid ethanol

Product 1

HCID 86585540HCID 86585540, compound

Procedure

(E)-2-(4-Phenylphenyl)ethenylpyridine-4-carboxylic acid (3.60 g) and a mixture of concentrated sulfuric acid/ethanol (9:1) were refluxed under heating for 2 hr, and neutralized under ice-cooling. The reaction mixture was partitioned between dichloromethane and water, and the aqueous layer was extracted once with dichloromethane. The organic layers were combined, dried over magnesium sulfate and concentrated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1-4/1) to give the objective compound (3.14 g) as a white solid.

Workup

  1. temperaturewere refluxed
  2. temperatureunder heating for 2 hr
  3. temperaturecooling
  4. customThe reaction mixture was partitioned between dichloromethane and water
  5. extractionthe aqueous layer was extracted once with dichloromethane
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1-4/1)

Sources & evidence

ORD record
ord-9f42b557e36447e681a6e0cd38d388d2
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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