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

HRID 450044

Reaction equation

HRID 450044 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.O>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

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 362195-Nitroindoline

Product 1

HCID 1677381H-Indole, 2,3-dihydro-1-methyl-5-nitro-Yield 92.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-nitro-2,3-dihydro-1H-indole (1 g, 6.09 mmol) in acetone (12 ml) was added powdered potassium hydroxide (1.7 g, 30.45 mmol), followed by methyl iodide (1.2 g, 9.14 mmol) and stirred overnight at ambient temperature. The solvent was evaporated under vacuum to give a residue, to which water was added and the product extracted with ethyl acetate. Drying and concentration of the organic layer yielded 1-methyl-5-nitro-2,3-dihydro-1H-indole (1 g, 92%) as solid.

Workup

  1. customThe solvent was evaporated under vacuum
  2. customto give a residue
  3. extractionthe product extracted with ethyl acetate
  4. customDrying

Sources & evidence

ORD record
ord-d7a933c1cbea496898453122ccff6b34
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Linked notes

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