Reacción #11470

Ecuación de reacción

MeOH CHCl3

2,4-dichloro-5,6-dimethyl-3-nitropyridine

triethylamine

1,2-diamino-2-methylpropane

→

N′-(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)-2-methylpropane-1,2-diamine

Rendimiento 57.6%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónthe reaction mixture was concentrated under reduced pressure
2. 2
   workup.ADDITIONThe resulting oil was treated with CH2Cl2 (200 mL) and H2O (100 mL)
3. 3
   workup.ADDITIONby addition of concentrated NH4OH solution
4. 4
   OtroThe layers were separated
5. 5
   Extracciónthe aqueous portion was extracted with an additional 100 mL of CH2Cl2
6. 6
   LavadoThe combined organic portions were washed with H2O (2×) and brine
7. 7
   SecadoThe organic portion was dried with Na2SO4
8. 8
   Concentraciónconcentrated
9. 9
   Otroto give an orange oil that solidified

Procedimiento

A stirred solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (4.42 g, 20.0 mmol) in 50 mL of anhydrous DMF, under N2, was treated with triethylamine (5.58 mL, 40.0 mol) and 1,2-diamino-2-methylpropane (2.10 mL, 20.0 mmol). After stirring for 24 h, the reaction mixture was concentrated under reduced pressure. The resulting oil was treated with CH2Cl2 (200 mL) and H2O (100 mL). The aqueous layer was made basic (pH-12) by addition of concentrated NH4OH solution. The layers were separated and the aqueous portion was extracted with an additional 100 mL of CH2Cl2. The combined organic portions were washed with H2O (2×) and brine. The organic portion was dried with Na2SO4 and concentrated to give an orange oil that solidified on standing. Column chromatography (SiO2, 2% MeOH/CHCl3) gave N′-(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)-2-methylpropane-1,2-diamine (3.14 g) as a yellow solid.

Fuente