HCID 13286896, compound → HCID 20183518, compound

HRID 255506Notes

Reaction equation

HRID 255506 reaction equation
[OH:1][C:2]1[C:3]([CH2:16][CH:17]=[CH2:18])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.[H][H]>C(O)C.[Pd]>[OH:1][C:2]1[C:3]([CH2:16][CH2:17][CH3:18])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2

Participants

5

Reactant 2

HCID 13286896HCID 13286896, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20183518HCID 20183518, compoundYield 74.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl 5-hydroxy-4-(2-propenyl)-1H-indole-2-carboxylate (2.16 g) was dissolved in dry ethanol (100 ml) and hydrogenated at atmospheric pressure in the presence of 5% palladium on charcoal (0.2 g) until hydrogen uptake had ceased. The catalyst was filtered off, washed with hot ethanol, the filtrate evaporated and the residue recrystallised from aqueous ethanol to give 1.616 g of the desired product mp 185°-186°:

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with hot ethanol
  3. customthe filtrate evaporated
  4. customthe residue recrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-41d336308f804bd6978774d771a50153
Source dataset
uspto-grants-1987_10
Patent number
US04698345

Reaction notes

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