3-Chloro-6-hydroxyacetophenone → (E)-1-(5-chloro-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one

HRID 46369Notes

Reaction equation

HRID 46369 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>CC(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])/[CH:9]=[CH:14]/[N:15]([CH3:17])[CH3:16])[CH:7]=1

Participants

4

Reactant 2

HCID 740613-Chloro-6-hydroxyacetophenoneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 33728788(E)-1-(5-chloro-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-oneYield 72%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 1-(5-chloro-2-hydroxyphenyl)ethanone (17.2 g, 100.8 mmol) in propan-2-ol (100 ml) was added 1,1-dimethoxy-N,N-dimethylmethanamine (27 ml, 200 mmol) dropwise and the reaction mixture was warmed to 45° C. and stirred for 24 hours. The resulting suspension was cooled in ice, filtered and washed with propan-2-ol then tert-butyl methyl ether. The solid was dried in vacuo to give the title compound as a bright yellow solid, 16.39 g, 72% yield.

Workup

  1. temperatureThe resulting suspension was cooled in ice
  2. filtrationfiltered
  3. washwashed with propan-2-ol
  4. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-8c94de01153b46b79422b55180ac0bde
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Reaction notes

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