2,4-Dimethylpyridine → HCID 22388276, compound

HRID 1072785Notes

Reaction equation

HRID 1072785 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-5572bfe7d6d74fe6b7266b48ae3b4ed8
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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