2,4-Dimethylpyridine → HCID 22388276, compound

HRID 1699805Notes

Reaction equation

HRID 1699805 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-phenyl benzaldehyde (6.45 g), 2,4-lutidine (7.59 g) and acetic anhydride (10 ml) was heated at a bath temperature of 150° C. for 12 hr, and refluxed under heating for 12 hr. The reaction mixture was concentrated under reduced pressure to dryness. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1-5/1) to give the objective compound (4.35 g) as a yellow solid.

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 12 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure to dryness
  4. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1-5/1)

Sources & evidence

ORD record
ord-08a1b95716a94892a3b5be1e8e0e22d8
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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