Methyl iodide → 6-Chloro-1-methyl-1H-indole

HRID 1449626Notes

Reaction equation

HRID 1449626 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[CH3:11]C(C)([O-])C.[K+].CI>O1CCCC1.O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH3:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 871116-ChloroindoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 153353216-Chloro-1-methyl-1H-indoleYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-chloroindole (22.0 g, 0.145 mole) and potassium t-butoxide (KOt-Bu) (20.0 g 0.179 mole) in tetrahydrofuran at room temperature is treated dropwise with methyl iodide (11.2 mL, 0.179 mole), allowed to stir at ambient temperatures for about 1 hour and diluted with a mixture of pet ether and water. The phases are separated. The organic phase is washed with 1 N HCL and water, dried over Na2SO4 and concentrated to a brown oil. After chromatography (silica gel/4:1 hexanes:ethyl acetate), the oil is distilled to afford the title product as a colorless oil, 16.25 g (67% yield), bp 110°-115° C./4 mm Hg, identified by IR, 1HNMR, 13CNMR, mass spectral and microanalyses.

Workup

  1. customThe phases are separated
  2. washThe organic phase is washed with 1 N HCL and water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to a brown oil
  5. distillationAfter chromatography (silica gel/4:1 hexanes:ethyl acetate), the oil is distilled

Sources & evidence

ORD record
ord-63e9fac71a434d04b514fa534a566916
Source dataset
uspto-grants-1997_02
Patent number
US05599832

Reaction notes

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