Hydrochloric Acid → HCID 12799934, compound

HRID 2412606Notes

Reaction equation

HRID 2412606 reaction equation
[CH2:1]([C:13]1[NH:14][C:15]2[C:20]([CH:21]=1)=[CH:19][C:18]([C:22]([OH:24])=[O:23])=[CH:17][CH:16]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].Cl>C(O)CCC>[CH2:1]([C:13]1[NH:14][C:15]2[C:20]([CH:21]=1)=[CH:19][C:18]([C:22]([O:24][CH2:13][CH2:1][CH2:2][CH3:3])=[O:23])=[CH:17][CH:16]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12797226HCID 12797226, compound

Product 1

HCID 12799934HCID 12799934, compoundYield 109.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 2-(n-dodecyl)indole-5-carboxylic acid (15.0 g) in n-butanol (100 ml) containing aqueous hydrochloric acid (10ml of strength 36.5% w/v) was heated on a steam bath for 8 hours. The solution was concentrated in vacuo to about one half of its volume, diethyl ether (300 ml) was added, and the solution was washed with water and was dried over magnesium sulphate. Evaporation of the solvent in vacuo gave a residue which was recrystallised from methanol to give n-butyl 2-(n-dodecyl)indole-5-carboxylate (9.6 g), in the form of an off-white powder, m.p. 74°-76° C.

Workup

  1. temperaturewas heated on a steam bath for 8 hours
  2. concentrationThe solution was concentrated in vacuo to about one half of its volume, diethyl ether (300 ml)
  3. additionwas added
  4. washthe solution was washed with water
  5. dry with materialwas dried over magnesium sulphate
  6. customEvaporation of the solvent in vacuo
  7. customgave a residue which
  8. customwas recrystallised from methanol

Sources & evidence

ORD record
ord-aa9bd4b0ff6248d59deaf9a20b6d9f53
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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