Perchloric Acid → HCID 12799997, compound

HRID 2412632Notes

Reaction equation

HRID 2412632 reaction equation
[C:1]([C:20]1[C:28]2[C:23](=[CH:24][C:25]([C:29]([OH:31])=[O:30])=[CH:26][CH:27]=2)[NH:22][CH:21]=1)(=O)[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].Cl(O)(=O)(=O)=O>C(O)(=O)C.[Pd]>[CH2:1]([CH:20]1[C:28]2[C:23](=[CH:24][C:25]([C:29]([OH:31])=[O:30])=[CH:26][CH:27]=2)[NH:22][CH2:21]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

5

Reactant 2

HCID 24247Perchloric AcidHCID 12797263HCID 12797263, compound

Product 1

HCID 12799997HCID 12799997, compoundYield 42.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

3-(n-Octadecanoyl)indole-6-carboxylic acid (20.5 g) in glacial acetic acid (300 ml), containing perchloric acid (13 ml, of strength 70% w/v), was hydrogenated over palladium on charcoal (3 g of 5% w/w) at atmospheric pressure and at a temperature of 80°-90° C. The mixture was then hot filtered through diatomaceous earth and was poured into water (1500 ml) to give an off-white solid. The solid was collected, washed with water (2×100 ml) and was dissolved in ethyl acetate (100 ml). The ethyl acetate solution was washed with an aqueous solution of sodium carbonate (of strength 2N, 150 ml) and the organic layer was separated and was dried over magnesium sulphate. The organic solvent was removed in vacuo to give (RS)-3-(n-octadecyl)indoline-6-carboxylic acid (8.5 g), in the form of an off-white solid, m.p. 112°-114° C.

Workup

  1. filtrationThe mixture was then hot filtered through diatomaceous earth
  2. additionwas poured into water (1500 ml)
  3. customto give an off-white solid
  4. customThe solid was collected
  5. washwashed with water (2×100 ml)
  6. dissolutionwas dissolved in ethyl acetate (100 ml)
  7. washThe ethyl acetate solution was washed with an aqueous solution of sodium carbonate (of strength 2N, 150 ml)
  8. customthe organic layer was separated
  9. dry with materialwas dried over magnesium sulphate
  10. customThe organic solvent was removed in vacuo

Sources & evidence

ORD record
ord-0eef744972d6462d8a402b89605b19b1
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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