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

HRID 461295

Reaction equation

HRID 461295 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 isopropylketone, 5 drops of acetic acid and 300 ml of ethanol was refluxed for 3 h, whereupon 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 h. 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 sodium hydroxide and extracted with ether. The dried extract was distilled in vacuo. Boiling point: 138°-142° C/8 mm Hg.

Workup

  1. temperaturewas refluxed for 3 h, whereupon the solvent
  2. customwas 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 h
  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-b9d6343300584789b1b97cb771b249e1
Source dataset
uspto-grants-1977_12
Patent number
US04062682

Linked notes

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