Perchloric Acid → HCID 12799980, compound

HRID 2412627Notes

Reaction equation

HRID 2412627 reaction equation
[C:1]([C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([C:29]([O:31][CH3:32])=[O:30])[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][CH:25]=[C:26]([C:29]([O:31][CH3:32])=[O:30])[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 12799957HCID 12799957, compound

Product 1

HCID 12799980HCID 12799980, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Methyl 3-(n-octadecanoyl)indole-5-carboxylate (17.30 g) was suspended in glacial acetic acid (400 ml), containing perchloric acid (11 ml, 70% w/v), and was hydrogenated over palladium on charcoal (5% w/w, 15 g) 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 (150 ml) to give an off-white solid. The solid was collected, washed with water (2×100 ml) and was dissolved in ethyl acetate (1000 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 sulfate. The organic solvent was removed in vacuo to give (RS)-methyl 3-(n-octadecyl)indoline-5-carboxylate in the form of an off-white solid, which was used without purification.

Workup

  1. filtrationThe mixture was then hot filtered through diatomaceous earth
  2. additionwas poured into water (150 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 (1000 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 sulfate
  10. customThe organic solvent was removed in vacuo

Sources & evidence

ORD record
ord-7a875ee599ea44659524f9c44b13334d
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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