Hydrogen Bromide → 4-[2-(Ethylamino)ethyl]benzene-1,2-diol;hydrobromide

HRID 2253612Notes

Reaction equation

HRID 2253612 reaction equation
[CH2:1]([NH:3][CH2:4][CH2:5][C:6]1[CH:15]=[CH:14][C:11]([O:12]C)=[C:8]([O:9]C)[CH:7]=1)[CH3:2].[BrH:16]>C(O)(=O)C>[BrH:16].[CH2:1]([NH:3][CH2:4][CH2:5][C:6]1[CH:15]=[CH:14][C:11]([OH:12])=[C:8]([OH:9])[CH:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 107509132-(3,4-Dimethoxyphenyl)-N-ethylethan-1-amine

Product 1

HCID 197459614-[2-(Ethylamino)ethyl]benzene-1,2-diol;hydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

After dissolving 1.0 g of N-ethyl-homoveratrylamine in a solvent mixture consisting of 6 ml of a 48% aqueous hydrogen bromide solution and 4 ml of acetic acid, the solution was heated at 120°-130° C. with stirring for 5 hours. The solvent was distilled off and the residue was crystallized from ether to obtain 1.2 g of crude crystals. N-Ethyl-3,4-dihydroxyphenethylamine hydrobromide having a melting point of 149°-151° C. was obtained by recrystallizing from isopropyl alcohol. The yield was 0.68 g.

Workup

  1. temperaturethe solution was heated at 120°-130° C.
  2. distillationThe solvent was distilled off
  3. customthe residue was crystallized from ether
  4. customto obtain 1.2 g of crude crystals

Sources & evidence

ORD record
ord-ee2a10da1d93467ba2d70052e60cf259
Source dataset
uspto-grants-1993_08
Patent number
US05232923

Reaction notes

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