Réaction #66588

Équation de réaction

Acetic acid trifluoroacetic acid

2-(3,4-dimethoxyphenyl)ethanamine

hexamethylenetetramine

→

title product

Rendement 95.0%

6,7-Dimethoxy-3,4-dihydroisoquinoline

Rendement 95.0%

Solvants

water

Conditions de réaction

Traitement

1. 1
   TempératureThe resulting solution was heated
2. 2
   Températureat reflux for about 5 hours in an oil bath
3. 3
   Extractionthe solution was extracted with dichloromethane (3×200 mL)
4. 4
   Séchagedried over anhydrous sodium sulfate
5. 5
   AutreSolids were removed by filtration
6. 6
   Concentrationthe resulting filtrate was concentrated in vacuo

Mode opératoire

Acetic acid/trifluoroacetic acid (100 mL) was added to a solution of 2-(3,4-dimethoxyphenyl)ethanamine (20 g, 110.38 mmol, 1.00 equiv) and hexamethylenetetramine (31 g, 221.11 mmol, 2.00 equiv). The resulting solution was heated at reflux for about 5 hours in an oil bath. After adding water (100 mL), the solution was extracted with dichloromethane (3×200 mL), and the organic layers were combined and dried over anhydrous sodium sulfate. Solids were removed by filtration, and the resulting filtrate was concentrated in vacuo to give the title product as a yellow oil (20 g, yield=95%). LC-MS: m/z=192 (MH)+.

Source