Acetone → 1H-Indole, 2-methyl-4-nitro-

HRID 2283680Notes

Reaction equation

HRID 2283680 reaction equation
[CH3:1][C:2]([CH3:4])=O.C(O[K])(C)(C)C.[N+:11]([C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17])([O-:13])=[O:12]>CS(C)=O.C(OCC)(=O)C>[CH3:1][C:2]1[NH:17][C:16]2[C:15]([CH:4]=1)=[C:14]([N+:11]([O-:13])=[O:12])[CH:20]=[CH:19][CH:18]=2

Participants

6

Reactant 3

HCID 180AcetoneHCID 74233-NitroanilineHCID 178418922HCID 178418922, compound

Product 1

HCID 110951501H-Indole, 2-methyl-4-nitro-

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acetone (1.0 mL) and tert-butoxy potassium (2.7 g) were added to a solution of 3-nitroaniline (1.38 g) in dimethylsulfoxide (20 ml), and the reaction solution was stirred at room temperature for 3 hours. The reaction solution was diluted with ethyl acetate, and washed successively with an aqueous ammonium chloride solution and a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum. The residue was purified by column chromatography on silica gel (developing solvent:hexane-ethyl acetate) to obtain 2-methyl-4-nitro-1H-indole.

Workup

  1. washwashed successively with an aqueous ammonium chloride solution
  2. dry with materialAfter drying over anhydrous sodium sulfate
  3. customthe solvent was evaporated under vacuum
  4. customThe residue was purified by column chromatography on silica gel (developing solvent:hexane-ethyl acetate)

Sources & evidence

ORD record
ord-e2ecb262ccc14118a3c587db2b791875
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

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