Water → HCID 19379420, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(3-furyl)-7-methoxy-2-quinolinone (4.1 g) from Step 1 in THF (250 mL) at reflux was added LiAlH4 (1M in THF; 68 mL). The mixture was refluxed for 50 hr., cooled to 0° C., and then treated successively with H2O (2.6 mL), 15% aq. NaOH (2.6 mL), and H2O (7.8 mL). The precipitate that formed was removed by filtration, washing with THF, and the tiltrate was concentrated and redissolved in MeCN (100 mL). To this solution at r.t. was added a solution of Ce(NH4)2 (NO3)6 (8.7 g) in H2O (30 mL). After the addition was complete, H2O (500 mL) was added and the resulting mixture extracted with EtOAc (3x). The combined organics were washed with H2O (2x) and brine, dried (MgSO4), and concentrated. Flash chromatography of the residue (silica gel; EtOAc/hexane (3:1)) provided 4-(3-furyl)-7-methoxyquinoline as a solid. A portion of this material (1.0 g) and pyridine hydrochloride (4 g) were heated at 175°-180° C. for 5 hr. While still hot, H2O (50 mL) and ice was added, causing the formation of a precipitate. Filtration and drying of this material provided the title compound as a solid.

Provenance & Evidence