2-(3-Benzyloxy-4-nitrophenyl)ethylamine, hydrochloride → 2-(4-Amino-3-benzyloxyphenyl)ethylamine, Hydrochloride

HRID 1032522Notes

Reaction equation

HRID 1032522 reaction equation
[ClH:1].[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH2:19][CH2:20][NH2:21])[CH:13]=[CH:14][C:15]=1[N+:16]([O-])=O)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>[Ni].CO>[ClH:1].[NH2:16][C:15]1[CH:14]=[CH:13][C:12]([CH2:19][CH2:20][NH2:21])=[CH:11][C:10]=1[O:9][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 1317165652-(3-Benzyloxy-4-nitrophenyl)ethylamine, hydrochloride

Product 1

HCID 221659982-(4-Amino-3-benzyloxyphenyl)ethylamine, Hydrochloride

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

In the presence of Raney nickel, 3.2 g of 2-(3-benzyloxy-4-nitrophenyl)ethylamine, hydrochloride, is hydrogenated in 50 ml of methanol, thus producing, after recrystallizing the product from ethanol, 1.36 g of 2-(4-amino-3-benzyloxyphenyl)ethylamine, hydrochloride, mp 181°-184° C.

Workup

  1. customthus producing
  2. customafter recrystallizing the product from ethanol, 1.36 g of 2-(4-amino-3-benzyloxyphenyl)ethylamine, hydrochloride, mp 181°-184° C.

Sources & evidence

ORD record
ord-78362eb093824b34a4414f82ea1384bc
Source dataset
uspto-grants-1990_09
Patent number
US04958026

Reaction notes

Loading…