2-Chloro-3,5-dinitropyridine → HCID 21103708, compound

Temperature

0 °C

2-chloro-3,5-dinitro-pyridine (27.36 g, 1) was divided into two equal portions and added into two 2 L round bottomed flasks. Methanol (700 mL) was then added to each flask. Nitrogen gas was bubbled through the solution while stirring and 7.15 g of 10% palladium on carbon was divided into two equal portions and added to each flask portion-wise under nitrogen. The solutions were cooled down under N2 to 0° C. using an ice-water bath. The N2 inlets were then replaced by hydrogen balloons. After evacuation, the solutions were exposed to H2 gas at slightly positive pressure. This vacuum-hydrogen exchange was done at least 5 times. The reactions were stirred under slight positive pressure of H2 for 2 days. Then the solutions were filtered with suction through Celite to remove the catalyst. The filtrate was concentrated down in vacuo. The crude product (24.27 g, >100% crude yield) was obtained as a dark green solid that was immediately used directly in the next step without further purification. The identity of the product (2) was confirmed by LC-MS.

1. customNitrogen gas was bubbled through the solution
2. additionadded to each flask portion-wise under nitrogen
3. stirringThe reactions were stirred under slight positive pressure of H2 for 2 days
4. filtrationThen the solutions were filtered with suction through Celite
5. customto remove the catalyst
6. concentrationThe filtrate was concentrated down in vacuo

ORD record

ord-1d0840d3eb7a4ef7a8ddc704d8a271e6

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07223759B2