2-Nitrophenethyl alcohol → Indole

HRID 845323Notes

Reaction equation

HRID 845323 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11]O)([O-])=O>[Ni].O1CCOCC1>[NH:1]1[C:4]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:10]=[CH:11]1

Participants

4

Reactant 1

HCID 270542-Nitrophenethyl alcohol

Product 1

HCID 798IndoleYield 1.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 312751,4-DioxaneSolvent

Procedure

A 120-ml autoclave was charged with 4.53 g (27.1 mmol) of 2-(o-nitrophenyl)ethanol, 15 ml of dioxane and 0.45 g (as metal) of "NDT-90" (Raney nickel catalyst of Kawaken Fine Chemicals Co., Ltd.). After purging the atmosphere in the autoclave with hydrogen, the pressure in the autoclave was increased to 30 kg/cm2 and reaction was conducted at 200° C. for 1 hour with agitation. The results were as follows: 100% conversion of 2-(o-nitrophenyl)ethanol, with an indole yield of 1.1%.

Workup

  1. customAfter purging the atmosphere in the autoclave with hydrogen
  2. temperaturethe pressure in the autoclave was increased to 30 kg/cm2 and reaction

Sources & evidence

ORD record
ord-7e6697d5c56e459188da4be01fa3b8fa
Source dataset
uspto-grants-1988_07
Patent number
US04757152

Reaction notes

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