Hydrochloric Acid → HCID 12398997, compound

HRID 1375330Notes

Reaction equation

HRID 1375330 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH:10](Br)[CH3:11])=[CH:5][CH:4]=1.[CH3:14][O:15][C:16]1[CH:21]=C[C:19](OC)=[CH:18][CH:17]=1.C[N:25](C)C1C=CC=CC=1.Cl>>[CH3:14][O:15][C:16]1[CH:21]=[C:11]2[C:19](=[CH:18][CH:17]=1)[NH:25][C:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[CH:10]2

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 90161,4-DimethoxybenzeneHCID 2991022-bromo-1-(4-methoxyphenyl)propan-1-one

Product 1

HCID 12398997HCID 12398997, compound

Procedure

A solution of p-methoxy-2-bromopropiophenone ((1 g, 4.11 mmol) was added to a solution of p-methoxyanisole in N,N dimethylaniline (1.7 g, 13.82 mmol)) and heated under reflux for 3 hours. The reaction mixture was cooled to room temperature, poured into 2N HCl, and extracted with EtOAc. The organic extract was washed with water and dried over Na2SO4. Removal of the solvent under reduced pressure and flash chromatography on SiO2 using CH2Cl2 gave the desired intermediate compound 2.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. extractionextracted with EtOAc
  4. extractionThe organic extract
  5. washwas washed with water
  6. dry with materialdried over Na2SO4
  7. customRemoval of the solvent under reduced pressure and flash chromatography on SiO2

Sources & evidence

ORD record
ord-eadc82c2aacf41dc89c5a51b5e812fce
Source dataset
uspto-grants-2007_01
Patent number
US07169611B2

Reaction notes

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