Dichloromethane → 7-methyl-6-nitro-1H-indole

HRID 1275655Notes

Reaction equation

HRID 1275655 reaction equation
[CH3:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH2:8][CH2:7]2.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>C1C=CC=CC=1>[CH3:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 11430Potassium CarbonateHCID 158963682,3-Dihydro-7-methyl-6-nitroindole

Product 1

HCID 158963777-methyl-6-nitro-1H-indoleYield 99.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 2,3-dihydro-7-methyl-6-nitroindole (3.1 g, 17.4 mmol) in 75 mL of benzene is treated with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ, 4.34 g, 19.1 mmol). The solution turns black and over the next 15 minutes, turns to green with a green precipitate. This mixture is distributed between 400 mL of aqueous potassium carbonate solution and 500 mL of methylene chloride. The organic solution is removed, dried over magnesium sulfate, filtered and evaporated to dryness on a rotary evaporator to afford 3.05 g of 7-methyl-6-nitroindole as a yellow solid (99% yield).

Workup

  1. customturns black and over the next 15 minutes
  2. customThe organic solution is removed
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness on a rotary evaporator

Sources & evidence

ORD record
ord-9a93b97dc3c147cb9fb6eea461d3c4e9
Source dataset
uspto-grants-2000_12
Patent number
US06162818

Reaction notes

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