Chloroform → 7-Chloro-5-nitro-1H-indole

HRID 2086038Notes

Reaction equation

HRID 2086038 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:11]([O-:13])=[O:12])[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(Cl)(Cl)Cl>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([N+:11]([O-:13])=[O:12])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 6212ChloroformHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 155414337-Chloro-2,3-dihydro-5-nitro-1H-indole

Product 1

HCID 154534647-Chloro-5-nitro-1H-indoleYield 79%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 7-chloro-5-nitroindoline (0.23 g, 1.2 mmol) in 20 mL of acetone was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone until color of the solution turns to dark green. Reaction mixture was concentrated in vacuo providing a dark residue which was subjected to column chromatography (CHCl3, neat) to yield 0.18 g (0.94 mmol, 79%) of the indole.

Workup

  1. customReaction mixture
  2. concentrationwas concentrated in vacuo
  3. customproviding a dark residue which

Sources & evidence

ORD record
ord-724e020447f442c5b8ea610c705479ad
Source dataset
uspto-grants-2004_04
Patent number
US06723741B2

Reaction notes

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