反应详情

Palladium (0.924 g, 0.868 mmol) was added to a three necked 1 L round bottom flask equipped with a condenser and flow of N2, and it was wet by adding a few mL of water. Then, N-methyl-3-nitropyridin-2-amine (19.0 g, 124 mmol) dissolved in ethanol (130 mL) was added. Hydrazine (15.41 ml, 496 mmol) was added to the above solution dropwise over a period of 20 minutes with continuous stirring. The reaction was exothermic, and H2 gas evolved during the reaction. The reaction mixture was stirred at room temperature for about 2 h. The color of the reaction changed from yellow to colorless. Completion of the reaction was checked by TLC. Pd was filtered on a tightly packed Celite® plug. The Celite® was first washed with DCM, and Pd was filtered off. A little bit of Celite®was placed on the top of Pd for safety, and it was washed with DCM until all the product was washed off of the Celite®. Combined solvent was concentrated and residue was taken in EtOAc washed with H2O. NaCl solid was added to remove any left over hydrazine. EtOAc was dried on Na2SO4, filtered and concentrated to give a dark brown solid (11.95 g; 78.25%).

1. customequipped with a condenser
2. additionwas added
3. customH2 gas evolved during the reaction
4. filtrationPd was filtered on a tightly packed Celite® plug
5. washThe Celite® was first washed with DCM, and Pd
6. filtrationwas filtered off
7. washwas washed with DCM until all the product
8. washwas washed off of the Celite®
9. concentrationCombined solvent was concentrated
10. washwashed with H2O
11. additionNaCl solid was added
12. customto remove
13. waitany left over hydrazine
14. dry with materialEtOAc was dried on Na2SO4
15. filtrationfiltered
16. concentrationconcentrated
17. customto give a dark brown solid (11.95 g; 78.25%)