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

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.

1. concentrationthe reaction mixture was concentrated under reduced pressure
2. additionThe resulting oil was treated with CH2Cl2 (200 mL) and H2O (100 mL)
3. additionby addition of concentrated NH4OH solution
4. customThe layers were separated
5. extractionthe aqueous portion was extracted with an additional 100 mL of CH2Cl2
6. washThe combined organic portions were washed with H2O (2×) and brine
7. dry with materialThe organic portion was dried with Na2SO4
8. concentrationconcentrated
9. customto give an orange oil that solidified

ORD record

ord-e0f5eb022f4447b49f0e2c6d141b3216

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07098221B2