Perchloric Acid → HCID 12799978, compound

HRID 2412642Notes

Reaction equation

HRID 2412642 reaction equation
[CH2:1]([C:12]1[NH:13][C:14]2[CH:15]=[CH:16][CH:17]=[C:18]([C:21]([OH:23])=[O:22])[C:19]=2[CH:20]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].Cl(O)(=O)(=O)=O.[H][H]>[Pd].C(O)(=O)C>[CH2:1]([CH:12]1[CH2:20][C:19]2[C:18]([C:21]([OH:23])=[O:22])=[CH:17][CH:16]=[CH:15][C:14]=2[NH:13]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 3

HCID 24247Perchloric AcidHCID 12797252HCID 12797252, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12799978HCID 12799978, compoundYield 73.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture containing 2-(n-undecyl)indole-4-carboxylic acid (25.8 g), palladium on charcoal (5% w/w, 5.2 g), 72% w/v aqueous perchloric acid (26 ml) and glacial acetic acid (200 ml) was heated by external application of steam while being shaken under an atmosphere of hydrogen. When the required hydrogen had been taken up, the hot mixture was filtered through diatomaceous earth, the residue was washed with fresh hot glacial acetic acid (200 ml), and the combined filtrates were concentrated in vacuo to about 75 ml. The residue was poured onto crushed ice and water, and 50% w/v aqueous sodium hydroxide was added to pH 12. Acetic acid was added to pH B 4-5 and the product was collected by filtration and washed with water. Recrystallisation from methanol yielded (RS)-2-(n-undecyl)indoline-4-carboxylic acid (19.1 g) in the form of a buff solid, m.p. 105°-108° C.

Workup

  1. temperaturewas heated by external application of steam
  2. filtrationthe hot mixture was filtered through diatomaceous earth
  3. washthe residue was washed with fresh hot glacial acetic acid (200 ml)
  4. concentrationthe combined filtrates were concentrated in vacuo to about 75 ml
  5. additionThe residue was poured
  6. customonto crushed ice and water, and 50%
  7. additionwas added to pH 12
  8. additionAcetic acid was added
  9. filtrationthe product was collected by filtration
  10. washwashed with water
  11. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-4b54617fb2964c1a9b224e11cb471b49
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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