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

HRID 2412611Notes

Reaction equation

HRID 2412611 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.[CH3:29]O>C(OCC)C.O1CCCC1>[CH2:1]([C:16]1[NH:17][C:18]2[C:23]([CH:24]=1)=[CH:22][C:21]([C:25]([O:27][CH3:29])=[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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 127972172-(n-Pentadecyl)indole-5-carboxylic acid

Product 1

HCID 12799917Methyl 2-(n-pentadecyl)indole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(n-pentadecyl)indole-5-carboxylic acid (15.0 g) in methanol (100 ml) containing aqueous hydrochloric acid (10 ml, of strength 36.5% w/v) was refluxed for 5 hours. After cooling, the mixture was dissolved in a mixture of diethyl ether and tetrahydrofuran (1:1). The solution was washed with water (2×50 ml), dried over sodium sulphate, evaporated in vacuo, and the residue was recrystallised from methanol to give methyl 2-(n-pentadecyl)indole-5-carboxylate (12.2 g), in the form of an off-white powder, m.p. 89°-92° C.

Workup

  1. temperaturewas refluxed for 5 hours
  2. temperatureAfter cooling
  3. washThe solution was washed with water (2×50 ml)
  4. dry with materialdried over sodium sulphate
  5. customevaporated in vacuo
  6. customthe residue was recrystallised from methanol

Sources & evidence

ORD record
ord-da739ee740fe452d8c8fbf67158944df
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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