Reacción #58586

Ecuación de reacción

NaOH H2O

anthranilonitrile

cyclopentylmagnesium bromide

HCl

→

crude product

Rendimiento 93.6%

2-aminophenyl cyclopentylmethanone

Rendimiento 93.6%

Disolventes

diethyl ether

diethyl ether

ethyl acetate

H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was stirred at room temperature for 1 hour
2. 2
   Extracciónto extract the aqueous layer
3. 3
   SecadoThe combined organic layers were dried over Na2SO4
4. 4
   OtroThe solvent was removed

Procedimiento

To a solution of anthranilonitrile (15.0 g) in diethyl ether (600 mL) was added a solution of 2.0 M cyclopentylmagnesium bromide in diethyl ether (159 mL) at 0° C. under nitrogen. The mixture was stirred at room temperature overnight (20 hours). 500 ml of 5 N HCl in H2O was added very slowly at 0° C. The mixture was stirred at room temperature for 1 hour. The aqueous layer was neutralized with 50% NaOH/H2O to pH=12. 2×500 mL of ethyl acetate was used to extract the aqueous layer. The combined organic layers were dried over Na2SO4. The solvent was removed to give the crude product 22.5 g (93.6% yield). H1NMR (CDCl3): δ6.62-7.82 (m, 4H), 3.64-3.78 (m, 1H), 1.50-1.96 (m, 8H).

Fuente