Ethanol → N-(1,2,3,4-tetrahydro-2-propyl-5-isoquinolinyl)-acetamide

HRID 48202

Reaction equation

HRID 48202 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]=[CH:9]2)([O-])=O.I[CH2:15][CH2:16][CH3:17].[CH3:18][CH2:19][OH:20]>>[CH2:15]([N:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][CH:12]=[CH:13][C:4]=2[NH:1][C:19](=[O:20])[CH3:18])[CH2:9]1)[CH2:16][CH3:17]

Participants

4

Reactant 3

HCID 702EthanolHCID 336431-IodopropaneHCID 690855-Nitroisoquinoline

Product 1

HCID 10376661N-(1,2,3,4-tetrahydro-2-propyl-5-isoquinolinyl)-acetamide

Procedure

A solution of 5-nitroisoquinoline (25 g, 0.144 mol) and iodopropane (36.7 g, 0.216 mol) in 500 mL of EtOH was converted to the title compound by the procedures described in Example 1. The crude title compound was purified by chromatography (silica gel, 95:5 EtOAc:EtOH). The purified product was recrystallized from iPr2O/THF to give the title compound as a white solid (3.33 g, 18%), mp=123° C.

Sources & evidence

ORD record
ord-6b284eb5fb784751a6f68a70a1b7e4ac
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Linked notes

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