Perchloric Acid → HCID 12799996, compound

HRID 2412631Notes

Reaction equation

HRID 2412631 reaction equation
[CH2:1]([C:13]1[C:21]2[C:16](=[CH:17][C:18]([C:22]([OH:24])=[O:23])=[CH:19][CH:20]=2)[NH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].Cl(O)(=O)(=O)=O>C(O)(=O)C.[Pd]>[CH2:1]([CH:13]1[C:21]2[C:16](=[CH:17][C:18]([C:22]([OH:24])=[O:23])=[CH:19][CH:20]=2)[NH:15][CH2:14]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 24247Perchloric AcidHCID 12797256HCID 12797256, compound

Product 1

HCID 12799996HCID 12799996, compoundYield 48.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

3-(n-Dodecyl)indole-6-carboxylic acid (16.1 g) in suspension in glacial acetic acid (200 ml), containing perchloric acid (12.2 ml; of strength (70% w/v) was hydrogenated over palladium on charcoal (1.8 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 (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 sulphate. The organic solvent was removed in vacuo to give (RS)-3-(n-dodecyl)indoline-6-carboxylic acid (7.9 g), in the form of a white solid (m.p. 100°-102° 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 (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 sulphate
  10. customThe organic solvent was removed in vacuo

Sources & evidence

ORD record
ord-c547083cf6644b69928d88b88b18df8b
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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