Reaktion #496467

Reaktionsgleichung

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

copper (I) cyanide

→

title compound

Ausbeute 82.7%

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

Ausbeute 82.7%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for ten minutes before it
2. 2
   Sonstigequenched with water and ethyl acetate
3. 3
   FiltrationThe slurry was filtered
4. 4
   WaschenThe organic layer was washed with water, brine
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   Einengenconcentrated in vacuo
7. 7
   Sonstigethe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes

Vorschrift

A mixture of 1-bromo-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester (1.02 g, 2.63 mmol), copper (I) cyanide (470 mg, 5.25 mmol) and anhydrous dimethylformamide (8.8 mL) was refluxed for ten minutes before it was cooled to room temperature quenched with water and ethyl acetate. The slurry was filtered. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate, concentrated in vacuo and the residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes to give the title compound as a yellow solid (727 mg): MS: (+) m/z 334.83 (M+1).

Quelle