3-Methyl-2-butanone → 5-Methoxy-2,3,3-trimethyl-3H-indole

HRID 1729580Notes

Reaction equation

HRID 1729580 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.[CH3:11][C:12]([CH:14]([CH3:16])[CH3:15])=O>C(O)(=O)C.C(O)C>[CH3:11][C:12]1[C:14]([CH3:16])([CH3:15])[C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=2[N:9]=1

Participants

5

Reactant 2

HCID 112513-Methyl-2-butanoneHCID 77023(4-Methoxyphenyl)hydrazine

Product 1

HCID 110953925-Methoxy-2,3,3-trimethyl-3H-indole

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.18 mole of 4-methoxy-phenylhydrazine, 0.27 mole of methyl-isopropyl ketone, five drops of acetic acid and 300 ml of ethanol was refluxed for 3 hours and then the solvent was evaporated. The dark residue (28 g of hydrazone) was dissolved in 125 ml of ethanol. After adding 54 ml of a 15 % by weight solution of concentrated sulphuric acid in ethanol the mixture was refluxed for 2.5 hours. The white precipitate (ammonium sulphate was filtered and the filtrate was diluted with 750 ml of water, neutralized with a few ml of aqueous 5N NaOH and extracted with ether. The dried extract was distilled in vacuo.

Workup

  1. temperaturewas refluxed for 3 hours
  2. customthe solvent was evaporated
  3. dissolutionThe dark residue (28 g of hydrazone) was dissolved in 125 ml of ethanol
  4. additionAfter adding 54 ml of a 15 % by weight solution of concentrated sulphuric acid in ethanol the mixture
  5. temperaturewas refluxed for 2.5 hours
  6. filtrationThe white precipitate (ammonium sulphate was filtered
  7. additionthe filtrate was diluted with 750 ml of water
  8. extractionextracted with ether
  9. extractionThe dried extract
  10. distillationwas distilled in vacuo

Sources & evidence

ORD record
ord-ddd57539c689469bb1b4a660820105ee
Source dataset
uspto-grants-1976_11
Patent number
US03989522

Reaction notes

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