4-allyl-5-hydroxy-N-(4-chlorophenyl)indole → 5-hydroxy-4-propyl-N-(4-chlorophenyl)indole

HRID 342769Notes

Reaction equation

HRID 342769 reaction equation
[CH2:1]([C:4]1[C:12]([OH:13])=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[CH:2]=[CH2:3]>C(OCC)(=O)C.[Pd]>[OH:13][C:12]1[C:4]([CH2:1][CH2:2][CH3:3])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[CH:7]=[CH:6]2

Participants

4

Reactant 1

HCID 541263834-allyl-5-hydroxy-N-(4-chlorophenyl)indole

Product 1

HCID 537470165-hydroxy-4-propyl-N-(4-chlorophenyl)indole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-allyl-5-hydroxy-N-(4-chlorophenyl)indole (Step C; 1.0 g, 3.54 mmol) was taken up in 25 mL ethyl acetate and hydrogenated (1 atm) at ambient temperature using 5% palladium on charcoal (40 mg) for 2 hours. The reaction was filtered through celite and concentrated in vacuo to provide the title compound which was used without further purification.

Workup

  1. customat ambient temperature
  2. customfor 2 hours
  3. filtrationThe reaction was filtered through celite and
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7539911006f84abd9c786bc8d010741f
Source dataset
uspto-grants-1999_01
Patent number
US05859051

Reaction notes

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