2-[2-(2-Methoxy-4-nitrophenoxy)ethyl]-1,2,3,4-tetrahydroisoquinoline → 4-[2-(3,4-dihydro-1H-isoquinolin-2-yl)ethoxy]-3-methoxyphenylamine

HRID 735143Notes

Reaction equation

HRID 735143 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[C:20]([N+:22]([O-])=O)[CH:19]=[CH:18][C:4]=1[O:5][CH2:6][CH2:7][N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1>ClCCl.CO>[CH2:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:16][CH2:17][N:8]1[CH2:7][CH2:6][O:5][C:4]1[CH:18]=[CH:19][C:20]([NH2:22])=[CH:21][C:3]=1[O:2][CH3:1]

Participants

3

Reactant 1

HCID 688163292-[2-(2-Methoxy-4-nitrophenoxy)ethyl]-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 688174124-[2-(3,4-dihydro-1H-isoquinolin-2-yl)ethoxy]-3-methoxyphenylamine

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 3.1.b. from 1.4 g (2.77 mmol) of 2-[2-(2-methoxy-4-nitrophenoxy)ethyl]-1,2,3,4-tetrahydroisoquinoline (65%). Yield: 1.2 g (94% of theory); C18H22N2O2 (M=298.38); calc.: molecular ion peak (M+H)+: 299; found: molecular ion peak (M+H)+: 299; Rf value: 0.5 (silica gel, dichloromethane/methanol (9:1)).

Workup

  1. customPrepared analogously to Example 3.1.b

Sources & evidence

ORD record
ord-6abb61bd40594f1da7d8b0815c8f9d00
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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