Water → HCID 58424870, compound

Participants

Reaction Steps

The compound of 9-methoxy-6-(4-methoxybenzyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridine-5(6H)-one (100 mg, 0.285 mmol) prepared in step 4 of Example 3 was dissolved in N,N-dimethylformamide (5 ml), added with sodium hydride (17 mg, 0.428 mmol) at 0° C. The reaction mixture was stirred for 1 hour at room temperature. After that, 1-bromopropane (0.039 ml, 0.428 mmol) was added and the mixture was stirred for one more hour at room temperature. The mixture was poured into water extracted with chloroform. The organic layer was washed with saturated sodium bicarbonate aqueous solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=1:1) to obtain the title compound (56 mg, yield: 50%, yellow solid).

Provenance & Evidence