Reacción #160754

Ecuación de reacción

2-(5,5-dimethyl-3-(3-nitropyridin-4-yl)cyclohex-2-enyl)isoindoline-1,3-dione

hydrogen

→

2-(3-(3-aminopyridin-4-yl)-5,5-dimethylcyclohex-2-enyl)isoindoline-1,3-dione

Rendimiento 89.0%

Disolventes

Acetic Acid

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroSolids were removed by filtration over celite
2. 2
   Lavadorinsed with EtOAc and MeOH
3. 3
   ConcentraciónThe filtrate was concentrated
4. 4
   workup.ADDITIONdiluted with EtOAc
5. 5
   Lavadowashed 2× with sat. aq. 2M Na2CO3
6. 6
   SecadoOrganic layer was dried with MgSO4
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated
9. 9
   OtroThe residue was purified by column (5% methanol in 1:1 ethyl acetate and hexanes)

Procedimiento

A solution of 2-(5,5-dimethyl-3-(3-nitropyridin-4-yl)cyclohex-2-enyl)isoindoline-1,3-dione (1 eq) in Acetic Acid (0.1M) was purged with nitrogen for 10 min. Then 10% Pd/C (0.10 eq) was added. The reaction mixture was stirred at room temperature overnight an atmosphere of hydrogen. Solids were removed by filtration over celite, then rinsed with EtOAc and MeOH. The filtrate was concentrated, diluted with EtOAc and washed 2× with sat. aq. 2M Na2CO3. Organic layer was dried with MgSO4, filtered, and concentrated. The residue was purified by column (5% methanol in 1:1 ethyl acetate and hexanes) to give 2-(3-(3-aminopyridin-4-yl)-5,5-dimethylcyclohex-2-enyl)isoindoline-1,3-dione (89%). LC/MS (m/z): MH+=348.3, Rt=0.79 min.

Fuente