Реакция #11470

Уравнение реакции

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

Выход 57.6%

Растворители

DMF

Условия реакции

Обработка

1. 1
   Концентрированиеthe 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
   ДругоеThe layers were separated
5. 5
   Экстракцияthe aqueous portion was extracted with an additional 100 mL of CH2Cl2
6. 6
   ПромывкаThe combined organic portions were washed with H2O (2×) and brine
7. 7
   СушкаThe organic portion was dried with Na2SO4
8. 8
   Концентрированиеconcentrated
9. 9
   Другоеto give an orange oil that solidified

Методика

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.

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