Ethanol → HCID 57901811, compound

HRID 1851348Notes

Reaction equation

HRID 1851348 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)=[CH:9]2)([O-])=O.C(O)C>[C].[Pd].O1CCCC1>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:10]1[NH:11][C:12]2[C:8]([CH:9]=1)=[CH:7][CH:6]=[CH:5][C:4]=2[NH2:1]

Participants

5

Reactant 2

HCID 702EthanolHCID 57901748HCID 57901748, compound

Product 1

HCID 57901811HCID 57901811, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-nitro-2-(pyridin-2-yl)-1H-indole (0.47 g), 10% palladium-carbon (50% water, 0.05 g), ethanol (4 mL) and tetrahydrofuran (10 mL) was stirred at room temperature overnight under a hydrogen atmosphere. Palladium-carbon was filtered off, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography and the title compound (0.35 g, yield 85%) was obtained as pale-yellow crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). melting point 165-166° C.

Workup

  1. filtrationPalladium-carbon was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ca3f6df1fd5747c9b3fd185960c49bf1
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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