Ethanol → HCID 57901870, compound

HRID 1851352Notes

Reaction equation

HRID 1851352 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[C:6]([N+:11]([O-])=O)[CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:14](=[O:17])[CH2:15][CH3:16].C(O)C>[C].[Pd].O1CCCC1>[NH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[NH:4][C:3]([C:14](=[O:17])[CH2:15][CH3:16])=[C:2]2[CH3:1]

Participants

5

Reactant 2

HCID 702EthanolHCID 57901646HCID 57901646, compound

Product 1

HCID 57901870HCID 57901870, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(3-methyl-7-nitro-1H-indol-2-yl)propan-1-one (0.29 g), 10% palladium-carbon (50% containing water, 0.03 g), ethanol (4 mL) and tetrahydrofuran (4 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 (0.17 g, yield 70%) was obtained as yellow crystals from a fraction eluted with tetrahydrofuran-hexane (1:1, volume ratio). melting point>194° C. (decomposition).

Workup

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

Sources & evidence

ORD record
ord-7a505aad61944118abcc395970728691
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

Loading…