Perchloric Acid → HCID 12799979, compound

HRID 2412644Notes

Reaction equation

HRID 2412644 reaction equation
[CH2:1]([C:21]1[NH:22][C:23]2[C:28]([CH:29]=1)=[CH:27][C:26]([C:30]([OH:32])=[O:31])=[CH:25][CH:24]=2)[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][CH2:18][CH2:19][CH3:20].Cl(O)(=O)(=O)=O>[Pd].C(O)(=O)C>[CH2:1]([CH:21]1[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([C:30]([OH:32])=[O:31])[CH:27]=2)[NH:22]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][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 2

HCID 24247Perchloric AcidHCID 12797224HCID 12797224, compound

Product 1

HCID 12799979HCID 12799979, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture containing 2-(n-eicosyl)indole-5-carboxylic acid (12.8 g), 5% w/w palladium on charcoal (2.0 g), 72% w/v aqueous perchloric acid (10 ml) and glacial acetic acid (150 ml) was heated by steam whilst shaken under hydrogen. Afterwards the mixture was filtered hot through diatomaceous earth, the residue was washed with hot glacial acetic acid (400 ml), and the combined filtrates were concentrated in vacuo to about 100 ml. The residue was poured into a mixture of ice and water, 50% w/v aqueous sodium hydroxide was added to pH 12 and acetic acid was then added to pH 4-5. The product was collected and recrystallised from methanol to give (RS)-2-(n-eicosyl)indoline-5-carboxylic acid hemimethanolate (4.8 g) as a pale brown solid. m.p. 110°-115° C.

Workup

  1. temperaturewas heated by steam
  2. filtrationAfterwards the mixture was filtered hot through diatomaceous earth
  3. washthe residue was washed with hot glacial acetic acid (400 ml)
  4. concentrationthe combined filtrates were concentrated in vacuo to about 100 ml
  5. additionThe residue was poured into a mixture of ice and water, 50%
  6. additionwas added to pH 12 and acetic acid
  7. additionwas then added to pH 4-5
  8. customThe product was collected
  9. customrecrystallised from methanol

Sources & evidence

ORD record
ord-cef7f9930d1b4d3089dc6afafa39f342
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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