Perchloric Acid → HCID 24839534, compound

HRID 2412634Notes

Reaction equation

HRID 2412634 reaction equation
[C:1]([C:10]1[C:18]2[C:13](=[CH:14][C:15]([C:19]([OH:21])=[O:20])=[CH:16][CH:17]=2)[NH:12][CH:11]=1)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Cl:22](O)(=O)(=O)=O>C(O)(=O)C.[Pd].C(OCC)(=O)C>[ClH:22].[CH2:1]([CH:10]1[C:18]2[C:13](=[CH:14][C:15]([C:19]([OH:21])=[O:20])=[CH:16][CH:17]=2)[NH:12][CH2:11]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 2

HCID 24247Perchloric AcidHCID 12797264HCID 12797264, compound

Product 1

HCID 24839534HCID 24839534, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(n-Octanoyl)indole-6-carboxylic acid (39.4 g) in glacial acetic acid (860 ml), containing perchloric acid (37 ml, of strength 70% w/v), was hydrogenated over palladium on charcoal (17 g of 5% w/w) at atmospheric pressure and at a temperature between 80°-90° C. The catalyst was removed by hot filtration through diatomaceous earth and on cooling a solid separated which was collected. The solid was washed with diethyl ether (2×100 ml) and was dissolved in ethyl acetate. The ethyl acetate solution was washed with an aqueous solution of sodium carbonate (2×100 ml of strength 2N) and was dried over magnesium sulphate and on evaporation in vacuo gave an off-white solid. The solid was dissolved in ethyl acetate (200 ml) and hydrogen chloride gas was bubbled through the solution. The resulting solid was collected and was washed with diethyl ether (2×200 ml) to give (RS)-3-(n-octyl)indoline-6-carboxylic acid hydrochloride (14.5 g), in the form of an off-white solid, m.p. 233°-234° C. with decomposition.

Workup

  1. customThe catalyst was removed by hot filtration through diatomaceous earth
  2. temperatureon cooling a solid
  3. customseparated which
  4. customwas collected
  5. washThe solid was washed with diethyl ether (2×100 ml)
  6. dissolutionwas dissolved in ethyl acetate
  7. washThe ethyl acetate solution was washed with an aqueous solution of sodium carbonate (2×100 ml of strength 2N)
  8. dry with materialwas dried over magnesium sulphate and on evaporation in vacuo
  9. customgave an off-white solid
  10. customhydrogen chloride gas was bubbled through the solution
  11. customThe resulting solid was collected
  12. washwas washed with diethyl ether (2×200 ml)

Sources & evidence

ORD record
ord-c8bed983e55c4c929ac9e60b1bdd258b
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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