반응 #46136

반응 방정식

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

potassium cyanide

potassium cyanide

→

titled product

수율 90.8%

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

수율 90.8%

용매

isopropanol

water

반응 조건

후처리

1. 1
   온도The solution was cooled to room temperature
2. 2
   기타partitioned between EtOAc and saturated NaHCO3 solution
3. 3
   추출The aqueous layer was extracted twice with EtOAc
4. 4
   세척the combined organic layers were washed with brine
5. 5
   건조dried over Na2SO4
6. 6
   여과filtered
7. 7
   농축concentrated in vacuo
8. 8
   기타The crude solid material was triturated with EtOAc/ether

실험 절차

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.

출처