Hydrochloric Acid → HCID 12398997, compound

HRID 2301261Notes

Reaction equation

HRID 2301261 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-3def2fc80867488f818c85d12d1174e2
Source dataset
uspto-grants-2002_12
Patent number
US06500669B1

Reaction notes

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