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

HRID 48201

Reaction equation

HRID 48201 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][CH3:16].[CH3:17][CH2:18][OH:19]>>[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:18](=[O:19])[CH3:17])[CH2:9]1)[CH3:16]

Participants

4

Reactant 3

HCID 702EthanolHCID 6340IodoethaneHCID 690855-Nitroisoquinoline

Product 1

HCID 10398491N-(2-ethyl-1,2,3,4-tetrahydro-5-isoquinolinyl)acetamide

Procedure

A solution of 5-nitroisoquinoline (25 g, 0.144 mol) in 250 mL of EtOH was treated with iodoethane (26.9 g, 0.172 mol) and the resulting solution heated at reflux for 24 hours. The reaction mixture was cooled and the material which formed was collected and dried. The material obtained was converted to the title compound by the procedures described in Example 1. A white solid was obtained (4.42 g, 17%).

Workup

  1. temperaturethe resulting solution heated
  2. temperatureat reflux for 24 hours
  3. temperatureThe reaction mixture was cooled
  4. customthe material which formed
  5. customwas collected
  6. customdried
  7. customThe material obtained

Sources & evidence

ORD record
ord-63374dd46e7b4aceb47f36df2ff1252c
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Linked notes

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