Réaction #46136

Équation de réaction

3-(bromomethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one

potassium cyanide

potassium cyanide

→

titled product

Rendement 90.8%

3-(Cyanomethyl)-6-methoxy-2-methyl-4-phenylisoquinolin

Rendement 90.8%

Solvants

isopropanol

water

Conditions de réaction

Traitement

1. 1
   TempératureThe solution was cooled to room temperature
2. 2
   Autrepartitioned between EtOAc and saturated NaHCO3 solution
3. 3
   ExtractionThe aqueous layer was extracted twice with EtOAc
4. 4
   Lavagethe combined organic layers were washed with brine
5. 5
   Séchagedried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated in vacuo
8. 8
   AutreThe crude solid material was triturated with EtOAc/ether

Mode opératoire

To a solution of 3-(bromomethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one (6.82 g, 19.0 mmol) in 100 mL of isopropanol was added a solution of potassium cyanide (2.48 g, 38.1 mmol) in 10 mL of water. The mixture was heated at 80° C. After one hour, another portion of potassium cyanide solution (300 mg in 5 mL of water) was added, and the reaction stirred for an additional hour. The solution was cooled to room temperature, and partitioned between EtOAc and saturated NaHCO3 solution. The aqueous layer was extracted twice with EtOAc, and the combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude solid material was triturated with EtOAc/ether to provide the titled product (5.01 g, 86% yield). HRMS (ES) exact mass calculated for C19H16N2O2 (M+H+): 305.1285. Found 305.1269.

Source