Reacción #496468

Ecuación de reacción

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

sodium hydroxide

→

title compound

Rendimiento 92.7%

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

Rendimiento 92.7%

Disolventes

methanol tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónwas concentrated
2. 2
   workup.ADDITIONWater (20 mL) was added
3. 3
   ExtracciónThe mixture was then extracted with dichloromethane and ethyl acetate
4. 4
   LavadoThe combined organic layers were washed with brine
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   Concentraciónconcentrated in vacuo

Procedimiento

To a mixture of 1-cyano-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester (727 mg, 2.18 mmol) and methanol/tetrahydrofuran (12.5 mL, 1:1.5) was added 2N sodium hydroxide (5.4 mL, 10.89 mmol) at room temperature. The yellow solution was stirred at that temperature for seventy minutes before it was concentrated. Water (20 mL) was added and the mixture was adjusted to pH=2 with 1N HCl (13 mL). The mixture was then extracted with dichloromethane and ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, concentrated in vacuo to give the title compound as a yellow solid (647 mg): MS: (+) m/z 320.80 (M+1).

Fuente