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

HRID 1258196Notes

Reaction equation

HRID 1258196 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-cdf4a1f7c32a4f538696a130f801404d
Source dataset
uspto-grants-2013_06
Patent number
US08466152B2

Reaction notes

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