Ammonium Chloride → 6-Chloro-N2,4-dimethyl-2,3-pyridinediamine

Temperature

85 °C

A flask was charged with 6-chloro-N,4-dimethyl-3-nitropyridin-2-amine (Step 109.2) (1 g, 4.96 mmol), Iron (1.385 g, 24.80 mmol) and 7N NH4Cl (21.26 mL, 149 mmol) in EtOH (40 mL) and the resulting mixture was heated up and stirred at 85° C. for 30 min. The reaction was filtered through a pad of Celite and volatils were removed under reduced pressure. The resulting aq. layer was extracted with CH2Cl2, the combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The crude paterial was purified by silica gel column chromatography (50% EtOAc/hexane) to afford the title product (660 mg, 3.85 mmol, 78% yield) as beige oil. tR: 0.74 min (LC-MS 2); ESI-MS: 172 [M+H]+ (LC-MS 2); Rf=0.39 (50% EtOAc/hexane); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.98 (s, 3H) 2.77 (d, J=4.7 Hz, 3H) 4.46 (s, 2H) 5.91 (d, J=4.3 Hz, 1H) 6.28 (s, 1H).

1. temperaturethe resulting mixture was heated up
2. filtrationThe reaction was filtered through a pad of Celite and volatils
3. customwere removed under reduced pressure
4. extractionThe resulting aq. layer was extracted with CH2Cl2
5. washthe combined organic layers were washed with brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated under reduced pressure
8. customThe crude paterial was purified by silica gel column chromatography (50% EtOAc/hexane)

ORD record

ord-95a80787c6614eea8803de45301af5de

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08975417B2