Reaktion #11470

Reaktionsgleichung

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

Ausbeute 57.6%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenthe 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
   SonstigeThe layers were separated
5. 5
   Extraktionthe aqueous portion was extracted with an additional 100 mL of CH2Cl2
6. 6
   WaschenThe combined organic portions were washed with H2O (2×) and brine
7. 7
   TrocknenThe organic portion was dried with Na2SO4
8. 8
   Einengenconcentrated
9. 9
   Sonstigeto give an orange oil that solidified

Vorschrift

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.

Quelle