1,2-Dimethylindole → 1-(1,2-dimethyl-1H-indol-3-yl)ethanone

HRID 1708602Notes

Reaction equation

HRID 1708602 reaction equation
CN(C)[C:3](=[O:5])[CH3:4].P(Cl)(Cl)(Cl)=O.[CH3:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[C:14]1[CH3:22]>>[C:3]([C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:13]([CH3:12])[C:14]=1[CH3:22])(=[O:5])[CH3:4]

Participants

4

Reactant 3

HCID 134081,2-DimethylindoleHCID 24813Phosphorus oxychlorideHCID 31374Dimethylacetamide

Product 1

HCID 2857551-(1,2-dimethyl-1H-indol-3-yl)ethanoneYield 80%

Procedure

To a solution of 6 moles of N,N-dimethylacetamide and cooled at 0° C., 1.5 moles of phosphorus oxychloride was added dropwise in 30 minutes with stirring. After further adding 1 mole of 1,2-dimethylindole thereto, the reaction was carried out at 85°-90° C. for 2 hours. Then, the reaction solution was poured into 2 liters of ice water. The reaction solution was made alkaline, extracted with 0.5 liter of ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue was recrystallized from ethyl acetate to give yellow crystals in yield of 80%.

Workup

  1. extractionextracted with 0.5 liter of ethyl acetate
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was recrystallized from ethyl acetate
  6. customto give yellow crystals in yield of 80%

Sources & evidence

ORD record
ord-ead1894bfcef416dbf89e976647c406a
Source dataset
uspto-grants-1994_10
Patent number
US05359085

Reaction notes

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