HCID 22388054, compound → HCID 86585540, compound

HRID 1699806Notes

Reaction equation

HRID 1699806 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 sulfite 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. customThe reaction mixture was partitioned between dichloromethane and water
  4. extractionthe aqueous layer was extracted once with dichloromethane
  5. dry with materialdried over magnesium sulfite
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1-4/1)

Sources & evidence

ORD record
ord-d2a01768f2fd4a41b11575ca25d72e33
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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