تفاعل #46136

معادلة التفاعل

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

potassium cyanide

potassium cyanide

→

titled product

المردود 90.8%

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

المردود 90.8%

المذيبات

isopropanol

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe solution was cooled to room temperature
2. 2
   أخرىpartitioned between EtOAc and saturated NaHCO3 solution
3. 3
   استخلاصThe aqueous layer was extracted twice with EtOAc
4. 4
   غسيلthe combined organic layers were washed with brine
5. 5
   تجفيفdried over Na2SO4
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated in vacuo
8. 8
   أخرىThe crude solid material was triturated with EtOAc/ether

الإجراء التجريبي

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.

المصدر