Water → 1-Methyl-6-nitro-1H-indole

HRID 2404633Notes

Reaction equation

HRID 2404633 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:13]([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:13][N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=2)[CH:8]=[CH:9]1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 785026-Nitro-1H-indole

Product 1

HCID 106073591-Methyl-6-nitro-1H-indoleYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-nitroindole (4.05 g 25 mmol) in DMF (50 mL) was added K2CO3 (8.63 g, 62.5 mmol) and Me (5.33 g, 37.5 mmol). After stirring at room temperature overnight, the mixture was poured into water and extracted with ethyl acetate. The combined organic layers were dried over Na2SO4 and concentrated under vacuum to give the product 1-methyl-6-nitro-1H-indole (4.3 g, 98%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-52a09b5401964c41a028ceb2689d8873
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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