4-Dimethylaminoacetophenone → (2E)-3-(dimethylamino)-1-[4-(dimethylamino)phenyl]prop-2-en-1-one

HRID 878548

Reaction equation

HRID 878548 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1>CN(C(OC)OC)C.C1(C)C=CC=CC=1.CC(O)=O>[CH3:1][N:2]([CH3:12])/[CH:3]=[CH:10]/[C:9]([C:6]1[CH:7]=[CH:8][C:3]([N:2]([CH3:1])[CH3:12])=[CH:4][CH:5]=1)=[O:11]

Participants

5

Reactant 1

HCID 750374-Dimethylaminoacetophenone

Product 1

HCID 71285027(2E)-3-(dimethylamino)-1-[4-(dimethylamino)phenyl]prop-2-en-1-oneYield 35.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 1140TolueneSolventHCID 78373Dimethylformamide dimethyl acetalSolvent

Procedure

A solution of 1-[4-(dimethylamino)phenyl]ethanone (500 mg, 3.1 mmol) in DMF-DMA (10 mL), toluene (10 mL), and AcOH (2 drops), was heated under reflux conditions for 48 h. The solution was concentrated and purified by flash column chromatography (hexanes:EtOAc=8:2˜1:1) to give the title compound (121 mg, 18%) as a yellow solid.

Workup

  1. concentrationThe solution was concentrated
  2. custompurified by flash column chromatography (hexanes:EtOAc=8:2˜1:1)

Sources & evidence

ORD record
ord-f40518ce670d40d89b47b89074166dc0
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Linked notes

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