Methyl iodide → 1H-Indole, 1-methyl-5-nitro-

HRID 450039Notes

Reaction equation

HRID 450039 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[OH-].[K+].[CH3:15]I>CC(C)=O>[CH3:15][N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[CH:7]=[CH:8]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 225235-Nitroindole

Product 1

HCID 1473221H-Indole, 1-methyl-5-nitro-Yield 92.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-nitro-1H-indole (2.0 g, 12.3 mmol) in acetone (20 ml), powdered potassium hydroxide (3.4 g, 60.7 mmol, 5 eq) was added followed by the addition methyl iodide (2.61 g, 18.5 mmol, 1.5 eq) at 0° C. The reaction mixture was heated to reflux for 10 hr. The solvent was evaporated and water was added. The compound was extracted with ethyl acetate, dried over anhydrous sodium sulphate, filtered and the organic layer was concentrated to dryness to yield 1-methyl-5-nitro-1H-indole (2.0 g, 92%). The crude compound was used in the next stage without purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 10 hr
  3. customThe solvent was evaporated
  4. additionwater was added
  5. extractionThe compound was extracted with ethyl acetate
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. concentrationthe organic layer was concentrated to dryness

Sources & evidence

ORD record
ord-d8e3e3273a2a424b9bffb4005c02104d
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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