Chloroform → 7-Chloro-2,3-dihydro-5-nitro-1H-indole

HRID 1489109Notes

Reaction equation

HRID 1489109 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH2:7]2)([O-:3])=[O:2].ClCl.C(Cl)(Cl)[Cl:16]>CC(O)=O>[Cl:16][C:11]1[CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[C:6]2[C:10]=1[NH:9][CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 6212ChloroformHCID 24526ChlorineHCID 362195-Nitroindoline

Product 1

HCID 155414337-Chloro-2,3-dihydro-5-nitro-1H-indole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 5-nitroindoline (0.5 g, 3.1 mmol) in 15 mL of AcOH was added a solution of Cl2 in AcOH dropwise until 30% of starting material was consumed. The reaction mixture was concentrated in vacuo, yielding an oil which was subjected to column chromatography (CHCl3, neat) to provide 0.23 g (1.2 mmol) of the desired product.

Workup

  1. customwas consumed
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customyielding an oil which

Sources & evidence

ORD record
ord-4fd6ec08c9b94c2e8d8233e6b6d2f05f
Source dataset
uspto-grants-1997_10
Patent number
US05677321

Reaction notes

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