2-Hydroxy-1,5-naphthyridine

Uses

1,5-Naphthyridin-2(1H)-one is used as a reactant in the design of brain penetrant JNK inhibitors for prevention of neurodegeneration.

Synthesis

The general procedure for the synthesis of 1,5-naphthyridin-2(1H)-one from the compound (CAS: 27017-69-2) was as follows: intermediate 2 (15.8 g) was dissolved in 6N hydrochloric acid solution (100 mL) and the reaction was stirred at 110 °C for 2 h. The reaction was carried out at 0 °C for 2 h. The reaction was carried out at 0 °C for 2 h. The solid was dried by suction filtration. Upon completion of the reaction, the reaction mixture was cooled to 0 °C and the pH was adjusted to 6-7 with solid sodium hydroxide. the precipitated solid was separated by filtration and dried by suction with a sintered funnel for 2 h, followed by vacuum drying at 45 °C to afford the target product 1,5-naphthyridin-2(1H)-one (14.4 g, 98% yield). [ES MS] m/z 147 (MH+).

References

[1] Patent: EP2080761, 2009, A1. Location in patent: Page/Page column 16
[2] Patent: WO2010/81874, 2010, A1. Location in patent: Page/Page column 18