HCID 12799989, compound → HCID 12797261, compound

HRID 2412629Notes

Reaction equation

HRID 2412629 reaction equation
[CH2:1]([CH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:28]([OH:30])=[O:29])[CH:26]=2)[NH:21][CH2:20]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>C1(C)C=C(C)C=C(C)C=1.[Pd]>[CH2:1]([C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:28]([OH:30])=[O:29])[CH:26]=2)[NH:21][CH:20]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 1

HCID 12799989HCID 12799989, compound

Product 1

HCID 12797261HCID 12797261, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7947MesityleneSolvent

Procedure

(RS)-3-(n-Octadecyl)indoline-5-carboxylic acid (2.0 g) in mesitylene (20 ml) was treated with palladium on charcoal (5% w/w, 0.15 g) and the mixture was refluxed for 2 hours. The catalyst was removed by hot filtration and the solvent was evaporated in vacuo to give a solid. The solid was recrystallised from methanol to give 3-(n-octadecyl)indole-5-carboxylic acid (1.10 g) in the form of a buff solid (m.p. 110°-112° C.).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customThe catalyst was removed by hot filtration
  3. customthe solvent was evaporated in vacuo
  4. customto give a solid
  5. customThe solid was recrystallised from methanol

Sources & evidence

ORD record
ord-387fe70ade3b40cc9fc1e0e10fe05359
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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