Reacción #496381

Ecuación de reacción

chloroform isopropanol

1-bromo-4-hydroxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester

copper(I) cyanide

dimethylformamide

→

title compound

Rendimiento 54.3%

1-Cyano-4-hydroxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester

Rendimiento 54.3%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas refluxed for ten minutes before it
2. 2
   Otrowere separated by filtration
3. 3
   LavadoThe organic layer of the filtrate was washed with water, and brine before it
4. 4
   Secadowas dried over anhydrous sodium sulfate
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroThe residue was purified by flash column chromatography on silica gel with a gradient of methanol and dichloromethane

Procedimiento

A mixture of 1-bromo-4-hydroxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester (1.22 g, 3.3 mmol), copper(I) cyanide (585 mg, 6.6 mmol), and anhydrous dimethylformamide (16 mL) was refluxed for ten minutes before it was cooled to room temperature and diluted with water. To the resulting slurry was added a chloroform/isopropanol mixture (3:1, 150 mL). After stirring for 10 minutes the solid components were separated by filtration and discarded. The organic layer of the filtrate was washed with water, and brine before it was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of methanol and dichloromethane to give the title compound as a white solid (574 mg): 1H NMR (CDCl3, 200 MHz): δ=12.26 (s, 1H), 8.15 (m, 1H), 7.71 (t, J=8.2 Hz, 1H), 7.38 (m, 2H), 7.17 (m, 4H), 4.12 (s, 3H).

Fuente