Methyl iodide → Methanone, (4-methoxyphenyl)(1-methyl-1H-indol-3-yl)-

HRID 247555Notes

Reaction equation

HRID 247555 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.[CH3:20][O-].[Na+].CI>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH3:20])[CH:10]=2)=[O:8])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 211017Ketone, indol-3-yl p-methoxyphenyl (6CI,8CI)HCID 10942334Sodium Methoxide

Product 1

HCID 3062676Methanone, (4-methoxyphenyl)(1-methyl-1H-indol-3-yl)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 g of compound 1 was dissolved in 30 ml of dimethylformamide and the solution was stirred at room temperature. 258 mg of sodium methoxide was added to the solution, followed by stirring for 30 minutes. Then,678 mg of methyl iodide was added dropwise to the solution and the reaction was continued for 1 hour. The reaction mixture was evaporated to dryness under reduced pressure, followed by addition of ethyl acetate and washing with water. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed. The obtained crude product was recrystallized from ethanol to give 3-(p-methoxybenzoyl)-N-methylindole (compound 8) in the form of white platy crystals. (Yield: 94%).

Workup

  1. stirringby stirring for 30 minutes
  2. customThe reaction mixture was evaporated to dryness under reduced pressure
  3. additionfollowed by addition of ethyl acetate
  4. washwashing with water
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was removed
  7. customThe obtained crude product
  8. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-184476bc710c44c18d24734065f486e5
Source dataset
uspto-grants-1987_11
Patent number
US04708961

Reaction notes

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