Nitric Acid → 4-Chloro-3-nitropyridin-2-amine
Reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH2:9])[CH:4]=1.S(=O)(=O)(O)O.[N+:15]([O-])([OH:17])=[O:16]>O>[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH2:9])[C:4]=1[N+:15]([O-:17])=[O:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
4-Chloro-2-pyridinamine hydrochloride (300 mg) was added portionwise to concentrated sulfuric acid (1.96 mL) at 4° C. To the mixture was added fuming nitric acid (0.1 mL) dropwise at 4° C. The mixture was stirred at ambient temperature for 3 hours. To the solution was added water and the mixture was extracted with EtOAc. The extract was washed with water, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with EtOAc and n-hexane to give 4-chloro-3-nitro-2-pyridinamine (125 mg) as a yellow powder.