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

HRID 46373

Reaction equation

HRID 46373 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 93.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
45 °C

Procedure

1-(5-chloro-2-hydroxyphenyl)ethanone, (165 g, 0.967 mol) was slurried in 2-propanol (1000 mL) then 1,1-dimethoxy-N,N-dimethylmethanamine (258.28 mL, 1.93 mol) was added and the resulting yellow solution was stirred at 45° C. for 18 hours. The resulting suspension was cooled to room temperature and stirred for a further 48 hours. The solid was filtered off, washed with 2-propanol (2×200 mL) and then tert-butylmethyl ether (200 mL) then dried to give the title compound as a bright yellow solid, (204.59 g).

Workup

  1. temperatureThe resulting suspension was cooled to room temperature
  2. stirringstirred for a further 48 hours
  3. filtrationThe solid was filtered off
  4. washwashed with 2-propanol (2×200 mL)
  5. dry with materialtert-butylmethyl ether (200 mL) then dried

Sources & evidence

ORD record
ord-3cd59b2213e54bb1bba92245806c50d0
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Linked notes

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