2,4-Dimethylpyridine → HCID 22388276, compound

HRID 1066347Notes

Reaction equation

HRID 1066347 reaction equation
[C:1]1([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=1[CH3:22]>C(OC(=O)C)(=O)C>[CH3:21][C:18]1[CH:19]=[CH:20][N:15]=[C:16](/[CH:22]=[CH:11]/[C:10]2[CH:13]=[CH:14][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:8][CH:9]=2)[CH:17]=1

Participants

4

Reactant 2

HCID 79362,4-DimethylpyridineHCID 76689(1,1'-Biphenyl)-4-carboxaldehyde

Product 1

HCID 22388276HCID 22388276, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-phenylbenzaldehyde (6.45 g), 2,4-lutidine (7.59 g), and acetic anhydride (10 ml) was heated on a bath at 150° C. for 12 hours and then heated under reflux for 12 hours. The reaction mixture was concentrated to dryness under reduced pressure, and the resulting residue was purified by silica-gel column chromatography (eluent, hexane:ethyl acetate=9:1 to 5:1) to give 4.35 g of a yellow solid of (E)-4-methyl-2-(4-phenylphenyl)ethenylpyridine.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 12 hours
  3. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  4. customthe resulting residue was purified by silica-gel column chromatography (eluent, hexane:ethyl acetate=9:1 to 5:1)

Sources & evidence

ORD record
ord-295f597559cd40ba82a3e4a90146f64f
Source dataset
uspto-grants-2001_06
Patent number
US06242474B1

Reaction notes

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