HCID 11299248, compound → HCID 86741348, compound

HRID 1906229Notes

Reaction equation

HRID 1906229 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]>[Pd]>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:11]=2)[CH:6]=[CH:5]1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 11299248HCID 11299248, compound

Product 1

HCID 86741348HCID 86741348, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

An intimate mixture of 1-acetyl-2,3-dihydro-1H-indole-5-acetic acid, methyl ester (2.96 g) and 10% palladium on charcoal (50% moistened with water) (6.18 g) was heated at 200° for 11/2 h and the resulting solid was continuously extracted with chloroform (Soxhlet) for 2 h. Evaporation of the solvent gave an oil (1.21 g), which was purified by column chromatography on silica (Merck 7734; 138 g). Elution with ether-petroleum ether (1:1) gave the title compound (0.99 g) as an oil which was used in the next stage without further purification.

Workup

  1. temperaturewas heated at 200° for 11/2 h
  2. extractionthe resulting solid was continuously extracted with chloroform (Soxhlet) for 2 h
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-8667596563864b7bb0cfc222c20a4392
Source dataset
uspto-grants-1987_03
Patent number
US04650810

Reaction notes

Loading…