Reaktion #73994

Reaktionsgleichung

2-(2,4-dichlorobenzylamino)-1-(3-nitrophenyl)ethanol

intermediate 171.2

2-(2,4-dichlorobenzylamino)-1-(3-nitrophenyl)ethanol

sulfuric acid

→

6,8-dichloro-4-(3-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe resulting solution was stirred for 12 h at room temperature
2. 2
   SonstigeThe reaction was then quenched by the addition of water/ice
3. 3
   ExtraktionThe resulting solution was extracted with 2×50 mL of DCM
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   Einengenconcentrated under vacuum
6. 6
   SonstigeThis resulted in 300 mg (63%) of 6,8-dichloro-4-(3-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline as yellow oil

Vorschrift

To 2-(2,4-dichlorobenzylamino)-1-(3-nitrophenyl)ethanol (intermediate 171.2) (500 mg, 1.47 mmol, 1.00 equiv) in DCM (10 mL) was added conc. sulfuric acid (4 mL) dropwise with stirring at 0-5° C. The resulting solution was stirred for 12 h at room temperature. The reaction was then quenched by the addition of water/ice. The pH value of the solution was adjusted to 10 with sodium hydroxide. The resulting solution was extracted with 2×50 mL of DCM and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 300 mg (63%) of 6,8-dichloro-4-(3-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline as yellow oil.

Quelle