Methyl iodide → 1H-Indole, 2,3-dihydro-1-methyl-5-nitro-

HRID 450040

Reaction equation

HRID 450040 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH2:7]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)[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 362195-Nitroindoline

Product 1

HCID 1677381H-Indole, 2,3-dihydro-1-methyl-5-nitro-Yield 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 5-nitroindoline (1.0 g, 6.1 mmol) in acetone (12 ml), powdered potassium hydroxide (1.7 g, 30.5 mmol, 5 eq) was added followed by the addition of methyl iodide (1.2 g, 9.1 mmol, 1.5 eq) at 0° C. The reaction mixture was stirred at room temperature overnight. The solvent was evaporated and water was added and the compound was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to dryness to yield 1-methyl-5-nitro-2,3-dihydro-1H-indole (1.0 g, 92%). The crude compound was used in the next stage without purification.

Workup

  1. customThe solvent was evaporated
  2. additionwater was added
  3. extractionthe compound was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-dbef5ae2e9084970b97682d86da42dcd
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Linked notes

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