Methyl iodide → 4-Chloro-1-methyl-1H-indole

HRID 1155684

Reaction equation

HRID 1155684 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[OH-].[Na+].[CH3:13]I>C1C=CC=CC=1>[CH3:13][N:6]1[C:7]2[C:3](=[C:2]([Cl:1])[CH:10]=[CH:9][CH:8]=2)[CH:4]=[CH:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 913454-Chloroindole

Product 1

HCID 130487594-Chloro-1-methyl-1H-indole

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 60 g of 4-chloro-1H-indole, 400 ml of benzene, 200 ml of 50% sodium hydroxide solution, 68 g of n-tetrabutylammonium hydrogen sulfate and 68 ml of methyl iodide was stirred at 40° C. for 4 hours and was then cooled. The decanted aqueous phase was extracted with ethyl acetate and the combined organic phases were washed with aqueous sodium chloride, dried over magnesium sulfate and distilled to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with an 8-2 cyclohexanebenzene mixture to obtain 63.85 g of 1-methyl-4-chloro-1H-indole.

Workup

  1. temperaturewas then cooled
  2. extractionThe decanted aqueous phase was extracted with ethyl acetate
  3. washthe combined organic phases were washed with aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. distillationdistilled to dryness under reduced pressure
  6. customThe residue was chromatographed over silica gel
  7. washwas eluted with an 8-2 cyclohexanebenzene mixture

Sources & evidence

ORD record
ord-c455ac1d250d4d4b9ed770be0bfa4e25
Source dataset
uspto-grants-1982_06
Patent number
US04332808

Linked notes

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