2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-(Tert-butyl)-6-nitro-1H-indole

HRID 73920Notes

Reaction equation

HRID 73920 reaction equation
[C:1]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([N+:14]([O-:16])=[O:15])=[CH:10][CH:11]=2)[NH:6]1)([CH3:4])([CH3:3])[CH3:2].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O1CCOCC1>[C:1]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([N+:14]([O-:16])=[O:15])[CH:8]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 574701952-(tert-Butyl)-6-nitroindoline

Product 1

HCID 574701962-(Tert-butyl)-6-nitro-1H-indoleYield 80.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-tert-butyl-6-nitro-2,3-dihydro-1H-indole (2.0 g, 9.1 mmol) in 1,4-dioxane (20 mL) was added DDQ at room temperature. After refluxing for 2.5 h, the mixture was filtered and the filtrate was concentrated under vacuum. The residue was purified by column chromatography to give 2-tert-butyl-6-nitro-1H-indole (1.6 g, 80%).

Workup

  1. temperatureAfter refluxing for 2.5 h
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated under vacuum
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-f978194ce5ef4948baf31dac0edec27c
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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