Perchloric Acid → HCID 12799968, compound

HRID 2412615Notes

Reaction equation

HRID 2412615 reaction equation
[CH2:1]([C:11]1[NH:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[C:15]([C:20]([OH:22])=[O:21])[CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].Cl(O)(=O)(=O)=O.[H][H]>[Pd].C(O)(=O)C>[CH2:1]([CH:11]1[CH2:19][C:18]2[C:13](=[CH:14][C:15]([C:20]([OH:22])=[O:21])=[CH:16][CH:17]=2)[NH:12]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 24247Perchloric AcidHCID 12797238HCID 12797238, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12799968HCID 12799968, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2-(n-decyl)indole-6-carboxylic acid (62.5 g), perchloric acid (40 ml of strength 70% w/v) and glacial acetic acid (400 ml) were hydrogenated over palladium on charcoal (5% w/w, 8.0 g) at 80°-90° C. and atmospheric pressure. When hydrogen uptake had ceased (after 4 hours) the hot mixture was filtered and the residue was washed with hot (80° C.) glacial acetic acid (500 ml). The combined filtrates were concentrated in vacuo to 450 ml and were poured onto ice (1000 g). The mixture was adjusted to pH 9 by treatment with an aqueous solution of sodium hydroxide (strength 50% w/v) and was then adjusted to pH 4-5 with glacial acetic acid. The solid was collected, was washed with water (3×100 ml) and was dried. The solid was dissolved in boiling ethanol, treated with charcoal, and the solution was filtered. The filtrate was treated with an excess of a solution of hydrogen chloride in ethanol (90 ml of strength 37% w/v) and then the mixture was cooled and diluted with diethyl ether (750 ml). The solid was collected and treated as in Example 56 to give (RS)-2-(n-decyl)indoline-6-carboxylic acid (47.4 g), in the form of a buff solid, m.p. 123°-125° C.

Workup

  1. custom(after 4 hours)
  2. filtrationwas filtered
  3. washthe residue was washed with hot (80° C.) glacial acetic acid (500 ml)
  4. concentrationThe combined filtrates were concentrated in vacuo to 450 ml
  5. additionwere poured onto ice (1000 g)
  6. customThe solid was collected
  7. washwas washed with water (3×100 ml)
  8. customwas dried
  9. dissolutionThe solid was dissolved
  10. additiontreated with charcoal
  11. filtrationthe solution was filtered
  12. additionThe filtrate was treated with an excess of a solution of hydrogen chloride in ethanol (90 ml of strength 37% w/v)
  13. temperaturethe mixture was cooled
  14. additiondiluted with diethyl ether (750 ml)
  15. customThe solid was collected
  16. additiontreated as in Example 56

Sources & evidence

ORD record
ord-e3aa207f44d7447a97882306b62111c8
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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