Dimethyl Sulfate → 1-Methyl-7-benzoylindole

HRID 236367Notes

Reaction equation

HRID 236367 reaction equation
[C:1]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[CH:14]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(OC)(O[CH3:22])(=O)=O.[OH-].[K+]>CC(C)=O>[CH3:22][N:16]1[C:17]2[C:13](=[CH:12][CH:11]=[CH:10][C:9]=2[C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:14]=[CH:15]1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 10878711(1H-Indol-7-yl)(phenyl)methanone

Product 1

HCID 201894801-Methyl-7-benzoylindole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 8.57 g. (38.8 mmoles) of 7-benzoylindole, 5.38 g. (42.7 mmoles) of dimethyl sulfate and 5.12 g. of 85% potassium hydroxide in 40 ml. of acetone was heated to reflux for 75 minutes. The mixture was poured into 500 ml. of water and extracted with methylene chloride. The organic phase was separated, dried and concentrated. The residue was chromatographed on silica gel using methylene chloride-hexane as the eluant. The fractions containing the product were combined and concentrated to dryness, 6.5 g.

Workup

  1. additionA mixture of 8.57 g
  2. temperatureto reflux for 75 minutes
  3. additionThe mixture was poured into 500 ml
  4. extractionof water and extracted with methylene chloride
  5. customThe organic phase was separated
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel
  9. additionThe fractions containing the product
  10. concentrationconcentrated to dryness, 6.5 g

Sources & evidence

ORD record
ord-1e8d03e4135044db954668e7970b98d1
Source dataset
uspto-grants-1987_02
Patent number
US04644005

Reaction notes

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