Phosphorus oxychloride → 1-(5-Methyl-1-methyl-1H-indol-3-YL)-ethanone

HRID 1194350Notes

Reaction equation

HRID 1194350 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][N:7]1[C:15]2[C:10](=[CH:11][C:12]([CH3:16])=[CH:13][CH:14]=2)[CH:9]=[CH:8]1.[CH3:17][C:18](N(C)C)=[O:19]>>[CH3:6][N:7]1[C:15]2[C:10](=[CH:11][C:12]([CH3:16])=[CH:13][CH:14]=2)[C:9]([C:18](=[O:19])[CH3:17])=[CH:8]1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 31374Dimethylacetamide2×HCID 1413791,5-Dimethylindole

Product 1

HCID 212700661-(5-Methyl-1-methyl-1H-indol-3-YL)-ethanone

Procedure

Phosphoryl chloride (2.1 ml) was added dropwise to ice-cooled, dimethylacetamide (20 ml) and the solution was stirred at ca.0° for 10 min. A solution of 1,5-dimethyl-1H-indole (2.5 g) in dimethylacetamide (5 ml) was added, and the resulting solution was stirred at 85° for 2 h, then cooled, and partitioned between sodium carbonate (2N; 500 ml) and ethyl acetate (2×300 ml). The combined organic extracts were washed with water (300 ml), dried and evaporated in vacuo to give an oil, which was purified by FCC eluting with chloroform:hexane (1:1) to give the title comound as a solid (1.5 g), m.p. 119°-121°.

Workup

  1. temperaturecooled
  2. temperaturecooled
  3. custompartitioned between sodium carbonate (2N; 500 ml) and ethyl acetate (2×300 ml)
  4. washThe combined organic extracts were washed with water (300 ml)
  5. customdried
  6. customevaporated in vacuo
  7. customto give an oil, which
  8. customwas purified by FCC
  9. washeluting with chloroform:hexane (1:1)

Sources & evidence

ORD record
ord-cef90a3963b649b985bc2c4eba05b33d
Source dataset
uspto-grants-1989_03
Patent number
US04814344

Reaction notes

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