Hydrochloric Acid → n-Butyl 2-(n-pentadecyl)indole-5-carboxylate

HRID 2412608Notes

Reaction equation

HRID 2412608 reaction equation
[CH2:1]([C:16]1[NH:17][C:18]2[C:23]([CH:24]=1)=[CH:22][C:21]([C:25]([OH:27])=[O:26])=[CH:20][CH:19]=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][CH3:15].Cl>C(O)CCC>[CH2:1]([C:16]1[NH:17][C:18]2[C:23]([CH:24]=1)=[CH:22][C:21]([C:25]([O:27][CH2:16][CH2:1][CH2:2][CH3:3])=[O:26])=[CH:20][CH:19]=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][CH3:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 127972172-(n-Pentadecyl)indole-5-carboxylic acid

Product 1

HCID 12799935n-Butyl 2-(n-pentadecyl)indole-5-carboxylateYield 121.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 2-(n-pentadecyl)indole-5-carboxylic acid (17.4 g) in n-butanol (100 ml) containing aqueous hydrochloric acid (10 ml of strength 36.5% w/v) was heated in a steam bath for 18 hours. The solution was concentrated in vacuo to about one half of its volume and the residue was dissolved in diethyl ether. The ethereal solution was washed with water (2×50 ml) and was dried over magnesium sulphate. Evaporation of the solvent in vacuo gave a solid, which was recrystallised from light petroleum ether (b.p. 40°-60° C.) and then from methanol to give n-butyl 2-(n-pentadecyl)indole-5-carboxylate (12.2 g), in the form of a white powder, m.p. 79°-80° C.

Workup

  1. temperaturewas heated in a steam bath for 18 hours
  2. concentrationThe solution was concentrated in vacuo to about one half of its volume
  3. dissolutionthe residue was dissolved in diethyl ether
  4. washThe ethereal solution was washed with water (2×50 ml)
  5. dry with materialwas dried over magnesium sulphate
  6. customEvaporation of the solvent in vacuo
  7. customgave a solid, which
  8. customwas recrystallised from light petroleum ether (b.p. 40°-60° C.)

Sources & evidence

ORD record
ord-6b4987c599d44374bcfb92be60cb1899
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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