Reaktion #73955

Reaktionsgleichung

2-((2,4-dichlorobenzyl)(methyl)amino)-1-(3-nitrophenyl)ethanol

sodium hydroxide

→

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

Lösungsmittel

sulfuric acid

—

ice

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a 500-mL 3-necked round-bottom flask, was placed
2. 2
   ExtraktionThe resulting solution was extracted with 2×500 mL of ethyl acetate
3. 3
   Trocknendried over sodium sulfate
4. 4
   SonstigeThis resulted in 7 g (51%) of 6,8-dichloro-2-methyl-4-(3-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline as a yellow solid

Vorschrift

Into a 500-mL 3-necked round-bottom flask, was placed a solution of 2-((2,4-dichlorobenzyl)(methyl)amino)-1-(3-nitrophenyl)ethanol (14 g, 39.55 mmol, 1.00 equiv) in dichloromethane (140 mL), sulfuric acid (140 mL). The resulting solution was stirred overnight at room temperature. The reaction progress was monitored by LCMS. The resulting solution was diluted with 100 mL of ice. The pH value of the solution was adjusted to 8-9 with sat. sodium hydroxide (100 mL). The resulting solution was extracted with 2×500 mL of ethyl acetate and the organic layers combined and dried over sodium sulfate. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10-1:5). This resulted in 7 g (51%) of 6,8-dichloro-2-methyl-4-(3-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline as a yellow solid.

Quelle