Dimethyl Sulfate → 1-Methyl-7-benzoylindole

HRID 1788956Notes

Reaction equation

HRID 1788956 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-a6f8d127e254415abb12a1c578177af2
Source dataset
uspto-grants-1987_08
Patent number
US04686224

Reaction notes

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