Water → 2-(1-methyl-1H-indol-3-yl)acetonitrile

HRID 1587714Notes

Reaction equation

HRID 1587714 reaction equation
[OH-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]#[N:14])=[CH:4]1.[CH3:15]I.O>CO>[CH3:15][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]#[N:14])=[CH:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 351795Indole-3-acetonitrile

Product 1

HCID 106547202-(1-methyl-1H-indol-3-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

20 cm3 of 50% aqueous sodium hydroxide solution are added to a mixture of 7.8 g (0.05 mol) of 3-indolylacetonitrile, 14.2 g (0.1 mol) of methyl iodide and 0.83 g of a solution of Triton B in methanol at a rate such that the temperature of the reaction mixture does not exceed 35° C. (approximately 1 h 30 min), and the reaction mixture is then stirred for 3 hours at room temperature; thereafter, 100 cm3, of water are added while cooling and the mixture is extracted with diethyl ether, the ether extract is thereafter washed with water to neutrality, dried over sodium sulphate and then filtered, the ether is evaporated off and the residue is crystallised in a sufficient quantity of pentane; the solid thereby obtained is drained and then dried.

Workup

  1. customdoes not exceed 35° C.
  2. custom(approximately 1 h 30 min)
  3. temperaturewhile cooling
  4. extractionthe mixture is extracted with diethyl ether
  5. extractionthe ether extract
  6. washis thereafter washed with water to neutrality
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. customthe ether is evaporated off
  10. customthe residue is crystallised in a sufficient quantity of pentane
  11. customthe solid thereby obtained
  12. customdried

Sources & evidence

ORD record
ord-00870ba16f9a4133becfd73a2d020151
Source dataset
uspto-grants-1993_06
Patent number
US05219859

Reaction notes

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