Reacción #448579

Ecuación de reacción

4-Methylcyclohexanone

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

ammonia

→

solid

Rendimiento 73.0%

5,6,7,8-Tetrahydro-6-methyl-3-nitro-quinoline

Rendimiento 73.0%

Disolventes

CHCl3

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe solution was heated
2. 2
   Temperaturaat gentle reflux for 3 h
3. 3
   OtroEvaporation of the solvent
4. 4
   Otrogave an orange residue which
5. 5
   Otroflash chromatographed over silica gel (16 g)
6. 6
   Lavadoeluting with EtOAc/hexane (1:10)

Procedimiento

4-Methylcyclohexanone (170 mg, 1.52 mmol) was mixed with 1-methyl-3,5-dinitro-2-pyridone (300 mg, 1.51 mmol) in 1M methanolic ammonia (30 mL, 30 mmol). The solution was heated at gentle reflux for 3 h. Evaporation of the solvent gave an orange residue which was suspended in CHCl3 and flash chromatographed over silica gel (16 g) eluting with EtOAc/hexane (1:10) to afford a white solid (211 mg, 73% yield): mp 50°-52° C.

Fuente