Pyridine → HCID 67392996, compound

Participants

Reaction Steps

A mixture of the N-(7-benzyloxy-4-hydroxyquinolin-3-yl)butyramide prepared in Part E (2.97 g, 8.83 mmol), P2S5 (1.96 g, 4.41 mmol), and pyridine was placed under a nitrogen atmosphere and heated to reflux. The resulting solution was cooled and the excess P2S5 was quenched slowly with 10% aqueous Na2CO3 (10 mL). The reaction mixture was partitioned between water (40 mL) and CH2Cl2 (100 mL). The organic layer was washed with 0.1 M aqueous HCl (50 mL), dried over MgSO4, filtered and concentrated to yield a brownish-yellow solid. The solid was treated with boiling heptane (40 mL) and filtered. The filtrate was allowed to cool and a solid formed. The light yellow solid was isolated by filtration and washed with cold heptane to provide 7-benzyloxy-2-propylthiazolo[4,5-c]quinoline (1.74 g, 59%).

Provenance & Evidence