3-(2,6-dichloro-3-nitro-phenyl)-1-methyl-1H-[1,6]naphthyridin-2-one → 3-(3-amino-2,6-dichloro-phenyl)-1-methyl-1H-[1,6]naphthyridin-2-one

Participants

Reaction Conditions

Reaction Steps

To a suspended solution of 3-(2,6-dichloro-3-nitro-phenyl)-1-methyl-1H-[1,6]naphthyridin-2-one (1.55 g, 4.427 mmol) in EtOH (12 mL) is added a solution of Sn(II)Cl2 (3.80 g, 19.92 mmol) in HCl (con. 16 mL) at 75° C. After stirring for 30 minutes at 75° C., the mixture is diluted with EtOAc and neutralized with K2CO3 to a pH of 8. The organic layer is washed with saturated K2CO3, brine and dried, filtered and concentrated to give crude product. The crude product is purified by recrystallization with CH2Cl2/EtOAc/Hexane to give the titled intermediate as a solid (1.32 g, 93.15%).

Provenance & Evidence