HCID 21824976, compound → HCID 13094300, compound

HRID 544557Notes

Reaction equation

HRID 544557 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)=[CH2:12])=[CH:8][CH:7]=[CH:6][CH:5]=2>C(O)C.[Pd]>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[CH3:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 1

HCID 21824976HCID 21824976, compound

Product 1

HCID 13094300HCID 13094300, compoundYield 60.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution consisting of 1-(2-methyl-3-indolyl)-1-(3-pyridyl)ethylene (9.37 g.), prepared according to the procedure described in the Journal of Heterocyclic Chemistry, Vol. 9, p. 833 (1972), dissolved in ethanol (200 ml.) was hydrogenated at 2.5 atmospheric pressure in the presence of 10% palladium-on-charcoal catalyst. The resulting reaction mixture was then filtered to remove the catalyst and the filtrate subsequently evaporated under reduced pressure to afford a residue. Crystallization of the latter material from an ethyl acetate/petroleum ether (b.p. 60°-80° C.) mixture then gave pure 2-methyl-3-[1-(3-pyridyl)ethyl]indole (yield, 5.74 g.), m.p. 139°-141° C.

Workup

  1. customprepared
  2. customThe resulting reaction mixture
  3. filtrationwas then filtered
  4. customto remove the catalyst
  5. customthe filtrate subsequently evaporated under reduced pressure
  6. customto afford a residue
  7. customCrystallization of the latter material from an ethyl acetate/petroleum ether (b.p. 60°-80° C.) mixture

Sources & evidence

ORD record
ord-3ad4ad11aa8b41858c5206df7ff2c77a
Source dataset
uspto-grants-1984_05
Patent number
US04451472

Reaction notes

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