Reacción #448587

Ecuación de reacción

1-methyl-3,5-dinitro-2-pyridone

2,2-dimethyl-cyclopentanone

ammonia

→

solid

Rendimiento 24.0%

5,6-Dihydro-7,7-Dimethyl-3-nitro-cyclopenta[b]pyridine

Rendimiento 24.0%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas refluxed overnight
2. 2
   OtroThe solvent was removed in vacuo
3. 3
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
4. 4
   Otrochromatographed over silica gel (eluent 90:10 v/v ethyl acetate-hexane)

Procedimiento

A mixture of 1-methyl-3,5-dinitro-2-pyridone (0.8 g, 4.0 mmol), 2,2-dimethyl-cyclopentanone (0.45 g, 4.0 mmol) and ammonia solution (2.0M) in methanol (40 mL) was refluxed overnight. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate. The soluble portion was flash chromatographed over silica gel (eluent 90:10 v/v ethyl acetate-hexane) to give a yellow solid (0.183 g, 24% yield).

Fuente