Ethanol → 3-(2-Amino-ethyl)-5-bromo-1H-indole-2-carboxylic acid

HRID 1263263

Reaction equation

HRID 1263263 reaction equation
Cl.C([O:4][C:5]([C:7]1[NH:18][C:17]2[C:12](=[CH:13][C:14]([Br:19])=[CH:15][CH:16]=2)[C:8]=1[CH2:9][CH2:10][NH2:11])=[O:6])C.C(O)C.[OH-].[Na+]>C(O)(=O)C>[Br:19][C:14]1[CH:13]=[C:12]2[C:17]([NH:18][C:7]([C:5]([OH:6])=[O:4])=[C:8]2[CH2:9][CH2:10][NH2:11])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 13241174Ethyl-5-bromo-tryptamine-2-carboxylate hydrochloride

Product 1

HCID 7627893-(2-Amino-ethyl)-5-bromo-1H-indole-2-carboxylic acidYield 91%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.00 g. (2.87 mmoles) of ethyl-5-bromo-tryptamine-2-carboxylate hydrochloride are boiled for 2 hours in a mixture of 10 ml. of ethanol and 10 ml. of 4 n aqueous sodium hydroxide solution. The mixture is cooled with ice, acidified to pH 6 with glacial acetic acid, and the separated crystals are collected by filtration. 0.75 g. (91%) of 5-bromo-tryptamine-2-carboxylic acid are obtained; m.p.: 248°-249° C.

Workup

  1. temperatureThe mixture is cooled with ice
  2. filtrationthe separated crystals are collected by filtration

Sources & evidence

ORD record
ord-13e442916f0e46d4a4244f6fb020ee22
Source dataset
uspto-grants-1984_06
Patent number
US04456607

Linked notes

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