반응 #11470

반응 방정식

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

수율 57.6%

용매

DMF

반응 조건

후처리

1. 1
   농축the 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
   기타The layers were separated
5. 5
   추출the aqueous portion was extracted with an additional 100 mL of CH2Cl2
6. 6
   세척The combined organic portions were washed with H2O (2×) and brine
7. 7
   건조The organic portion was dried with Na2SO4
8. 8
   농축concentrated
9. 9
   기타to give an orange oil that solidified

실험 절차

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.

출처