Tetrahydrofuran → 6-Methoxy-5-methyl-1H-indole

HRID 881609Notes

Reaction equation

HRID 881609 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH2:10][C:11]#N)=[C:5]([N+:13]([O-])=O)[CH:4]=1.O1CCCC1>[C].[Pd].C(O)CCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6]([CH:10]=[CH:11][NH:13]2)=[CH:7][C:8]=1[CH3:9]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 58437287(4-Methoxy-5-methyl-2-nitrophenyl)acetonitrile

Product 1

HCID 198038376-Methoxy-5-methyl-1H-indoleYield 69.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 2631-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (4-methoxy-5-methyl-2-nitrophenyl)acetonitrile (0.24 g) in a mixed solvent of tetrahydrofuran (2 mL) and n-butanol (2 mL) was added palladium-carbon powder (0.043 g) under an argon atmosphere and this mixture was stirred at 60° C. under a hydrogen atmosphere for 36 hours. The insoluble material was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate) to give the title compound (0.13 g).

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a181347de52d43ae890ddfb6d439158e
Source dataset
uspto-grants-2015_03
Patent number
US08993616B2

Reaction notes

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