5-ethyl-6-nitro-2,3-dihydro-1H-indole → 5-ethyl-6-nitro-1H-indole

HRID 1403977Notes

Reaction equation

HRID 1403977 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[NH:8][CH2:7][CH2:6]2)[CH3:2]>C(Cl)Cl.O=[Mn]=O>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[NH:8][CH:7]=[CH:6]2)[CH3:2]

Participants

4

Reactant 1

HCID 574702055-ethyl-6-nitro-2,3-dihydro-1H-indole

Product 1

HCID 574702065-ethyl-6-nitro-1H-indoleYield 100.9%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-ethyl-6-nitroindoline (1.9 g, 9.9 mmol) in CH2Cl2 (30 mL) was added MnO2 (4.0 g, 46 mmol). The mixture was stirred at ambient temperature for 8 h. The solid was filtered off and the filtrate was concentrated to dryness to give 5-ethyl-6-nitro-1H-indole (1.9 g).

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-e9032c2d3c3841ada73c796cd1ab473c
Source dataset
uspto-grants-2014_12
Patent number
US08912199B2

Reaction notes

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