HCID 53677353, compound → 3-Methyl-2-(3-pyridyl)-1-indoleoctanoic acid

HRID 1633140Notes

Reaction equation

HRID 1633140 reaction equation
[C:1]([CH:4]=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH3:20])=[C:12]1[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)([OH:3])=[O:2]>C(O)C.[Pd]>[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH3:20])=[C:12]1[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)([OH:3])=[O:2]

Participants

4

Reactant 1

HCID 53677353HCID 53677353, compound

Product 1

HCID 1195533-Methyl-2-(3-pyridyl)-1-indoleoctanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-(7-Carboxyhept-6-enyl)-2-(3-pyridyl)-3-methylindole (10 mg) is dissolved in 1 ml of absolute ethanol with a catalytic amount of 10% palladium on charcoal and hydrogenated at 1 atmosphere pressure. After 3.5 hours, the catalyst is removed by filtration and washed with a few milliliters of ethanol. The combined filtrates are concentrated in vacuo to yield a colorless oil which crystallizes to give 1-(7-carboxyheptyl)-3-methyl-2-(3-pyridyl)indole of Example 1 (crude product has m.p. 110°-113°).

Workup

  1. customthe catalyst is removed by filtration
  2. washwashed with a few milliliters of ethanol
  3. concentrationThe combined filtrates are concentrated in vacuo
  4. customto yield a colorless oil which
  5. customcrystallizes

Sources & evidence

ORD record
ord-a7a5f6edd7834811a549e28ffa08f326
Source dataset
uspto-grants-1984_10
Patent number
US04478842

Reaction notes

Loading…