Hydrochloric Acid → HCID 178514871, compound

Participants

Reaction Steps

To a suspension of 4-hydroxy-1-(3-nitrophenyl)-1,8-naphthyridin-2 (1H)-one (1.13 g, 4 mmol, obtained in Synthetic Example 4 (3)) in DMF (16 ml) was added sodium hydride (about 60%, 384 mg, 9.6 mmol, 2.4 eq.), and the mixture was stirred until the production of hydrogen was completed. Next, after phenylacetyl chloride (742 mg, 4.8 mmol, 1.2 eq.) was added, the mixture was stirred at room temperature, followed by addition of water. After acidified with hydrochloric acid, it was filtered to give precipitates which were washed with water and suspended in DMF (16 mL) without further purification. To the suspension was added hydrazine monohydrate (80%, 448 μl, 11.2 mmol, 2.8 eq.), and the resultant mixture was stirred at 100 to 110° C. overnight. The reaction mixture was admixed with water, and filtered to give precipitates which were dried to afford 3-benzyl-5-(3-nitrophenyl)-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (714 mg, 45%).

Provenance & Evidence