8-(4-Nitrophenyl)imidazo[1,2-a]pyridine → Benzenamine,4-imidazo[1,2-a]pyridin-8-yl-
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]3[N:12]([CH:16]=[CH:17][N:18]=3)[CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=1)([O-])=O>C(O)(=O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:11]3[N:12]([CH:16]=[CH:17][N:18]=3)[CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:9]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Add 45 g of iron powder to a solution of 15 g (62.7 mmol) of the product from Example 19 in 400 ml of 75% acetic acid. Heat to 60°-70° C. for 2 hr. Filter the reaction mixture over celite and concentrate the filtrate to approximately 50 ml under vacuum. Neutralize the residue with saturated sodium carbonate solution and extract with three 200 ml portions of methylene chloride. Dry the combined extracts over sodium sulfate, treat with charcoal and remove the solvent in vacuo. Crystallize the residue from ether to provide the title compound.