Acetic Acid → 1-(3-hydroxy-1-methyl-1H-indol-2-yl)ethanone

HRID 436861Notes

Reaction equation

HRID 436861 reaction equation
[OH:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH3:11])[C:3]=1[C:12](=[O:18])[CH2:13]S(C)(=O)=O.C(O)(=O)C>[Zn].C(O)C>[CH3:13][C:12]([C:3]1[N:4]([CH3:11])[C:5]2[C:10]([C:2]=1[OH:1])=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:18]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 125113181-(3-hydroxy-1-methyl-1H-indol-2-yl)-2-(methylsulfonyl)ethanone

Product 1

HCID 47121911-(3-hydroxy-1-methyl-1H-indol-2-yl)ethanone

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

A mixture of 17.0 g (0.0637 mole) 1-(3-hydroxy-1-methyl-1H-indol-2-yl)-2-(methylsulfonyl) ethanone, 21.0 g (0.32 mole) zinc dust, 40 ml glacial acetic acid and 80 ml ab. ethanol was stirred vigorously and heated at 45°-50° for 1 hour. After stirring an additional hour at room temperature, the mixture was filtered through diatomaceous earth and the filter cake washed several times with fresh ethanol. The combined filtrates were condensed to 150 ml and 50 ml of hot water was added. Cooling yielded a green solid which was filtered, washed with cold water and recrystallized from 70% aqueous methanol to yield green needles of mpt. 119°-121°.

Workup

  1. temperatureheated at 45°-50° for 1 hour
  2. filtrationthe mixture was filtered through diatomaceous earth
  3. washthe filter cake washed several times with fresh ethanol
  4. customcondensed to 150 ml and 50 ml of hot water
  5. additionwas added
  6. temperatureCooling
  7. customyielded a green solid which
  8. filtrationwas filtered
  9. washwashed with cold water
  10. customrecrystallized from 70% aqueous methanol
  11. customto yield green needles of mpt
  12. custom119°-121°

Sources & evidence

ORD record
ord-78b4ad755a9e4e03a43fc4219ffaa9a4
Source dataset
uspto-grants-1977_06
Patent number
US04028383

Reaction notes

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