Methyl iodide → 2-(2-Methoxy-4-methylphenyl)-1H-indole

HRID 839491Notes

Reaction equation

HRID 839491 reaction equation
[CH3:1][O-].[Na+].CI.[OH:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[C:14]1[NH:15][C:16]2[C:21]([CH:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2>CN(C)C=O>[CH3:1][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[C:14]1[NH:15][C:16]2[C:21]([CH:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 20323045HCID 20323045, compound

Product 1

HCID 203230552-(2-Methoxy-4-methylphenyl)-1H-indoleYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At a temperature of 25° C. 54 g (1 mol) of sodium methylate and 170 g (1.2 mol) of methyl iodide were added to a solution of 223 g (1 mol) of 2-(2'-hydroxy-4'-methyl-phenyl)-indole, prepared as in Example 1, in 1200 ml of N,N-dimethylformamide. The solution was then stirred for 2 hours and the crude product was precipitated by adding water. After recrystallization from benzene, 166 g of 2-(2'-methoxy-4'-methyl-phenyl)-indole were obtained. M.P.: 125° C. Yield: 70%.

Workup

  1. customAt a temperature of 25° C
  2. customthe crude product was precipitated
  3. additionby adding water
  4. customAfter recrystallization from benzene

Sources & evidence

ORD record
ord-76d4dfc90e164b8ea2cf9589998261d4
Source dataset
uspto-grants-1978_06
Patent number
US04096112

Reaction notes

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