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

HRID 2189537Notes

Reaction equation

HRID 2189537 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-d6e0ad906b6d4899af99d6c65a7055bf
Source dataset
uspto-grants-2012_12
Patent number
US08324242B2

Reaction notes

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