HCID 54337531, compound → HCID 13424126, compound

HRID 1980880Notes

Reaction equation

HRID 1980880 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH:7]=[CH:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH3:18])[C:10]=1[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)([OH:3])=[O:2]>C(O)C.[Pd]>[CH3:18][N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:1]([OH:3])=[O:2])=[C:10]1[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 1

HCID 54337531HCID 54337531, compound

Product 1

HCID 13424126HCID 13424126, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-(5-carboxypent-1-enyl)-1-methyl-2-(3-pyridyl)indole (0.51 g) in absolute ethanol (20 ml), to which is added 10% Pd/C (0.05 g), is hydrogenated at 3 atmospheres pressure for 2 hours. The catalyst is removed by filtration and the filtrate concentrated to dryness. Trituration of the residue with absolute ethanol gives a while solid, m.p. 117°-120°. Recrystallization from acetonitrile yields 1-methyl-2-(3-pyridyl)-3-(5-carboxypentyl)indole (the compound of Example 3), m.p. 128°-130°.

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate concentrated to dryness
  3. customTrituration of the residue with absolute ethanol gives a while solid, m.p. 117°-120°
  4. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-5e714f24411a489193bf4992667dd83f
Source dataset
uspto-grants-1985_04
Patent number
US04511573

Reaction notes

Loading…