HCID 54218001, compound → HCID 20270202, compound

HRID 485353Notes

Reaction equation

HRID 485353 reaction equation
[CH2:1]([O:3][C:4]([CH:6]=[CH:7][CH:8]=[CH:9][C:10]1[N:11]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:5])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[N:11]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 54218001HCID 54218001, compound

Product 1

HCID 20270202HCID 20270202, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1.1 g of 2-[4-(ethoxycarbonyl)butadienyl)-N-(3-pyridyl)indole in 25 ml of 95% ethanol is hydrogenated at 3 atmospheres pressure with 0.2 g of 10% palladium on charcoal for 31/2 hours. The reaction mixture is filtered through celite and evaporated to yield 2-[4-(ethoxycarbonyl)butyl)-N-(3-pyridyl)indole as a yellow oil; Rf (15% ethyl acetate in toluene/silica gel)=0.65; IR (CH2Cl2) 1726 cm-1.

Workup

  1. custom2 hours
  2. filtrationThe reaction mixture is filtered through celite
  3. customevaporated

Sources & evidence

ORD record
ord-82a528a9696345ccbd79bbb819b3df59
Source dataset
uspto-grants-1985_08
Patent number
US04536505

Reaction notes

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