Water → 1-methyl-1H-indole-7-carbaldehyde

HRID 2360478Notes

Reaction equation

HRID 2360478 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH:10]=[O:11])[CH:3]=[CH:2]1.[K].[CH3:13]C(C)([O-])C.CI.O>CN(C)C=O.C(OCC)(=O)C>[CH3:13][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH:10]=[O:11])[CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 2734629Indole-7-carboxaldehydeHCID 50987170Potassium tertbutoxide

Product 1

HCID 110409791-methyl-1H-indole-7-carbaldehyde

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

20 g 1H-indole-7-carbaldehyde are dissolved in 160 ml N,N-dimethylformamide and combined batchwise with 15.5 g potassium-tert.-butoxide under argon. After the addition has ended the mixture is left for 20 minutes with stirring and then 8.7 ml methyl iodide are added dropwise. Then the mixture is left for 12 hours at ambient temperature with stirring and then distributed between water and ethyl acetate. The aqueous phase is twice extracted with ethyl acetate and the combined organic phases are washed with saturated aqueous sodium chloride solution. After drying with magnesium sulphate the solvents are eliminated in vacuo. The residue is extracted from water. The solid thus obtained is suction filtered and dried in vacuo.

Workup

  1. additionAfter the addition
  2. waitThen the mixture is left for 12 hours at ambient temperature
  3. stirringwith stirring
  4. extractionThe aqueous phase is twice extracted with ethyl acetate
  5. washthe combined organic phases are washed with saturated aqueous sodium chloride solution
  6. dry with materialAfter drying with magnesium sulphate the solvents
  7. extractionThe residue is extracted from water
  8. customThe solid thus obtained
  9. filtrationfiltered
  10. customdried in vacuo

Sources & evidence

ORD record
ord-5b70bf3d9a4b48658fd1e630b6837274
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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