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0 °C

A solution of 1,6-naphthyridin-5(6H)-one (500 mg, 3.42 mmol) in POCl3 (10 mL) was stirred at 100° C. for 14 h. POCl3 was removed under reduced pressure. The residue was dissolved with DCM (40 mL), and the solution was stirred at 0° C. Then aqueous Na2CO3 was added cautiously to adjust pH to 6-7. Then the organic phase was separated from the aqueous phase, and the aqueous phase was extracted with EtOAc (4×15 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give 5-chloro-1,6-naphthyridine as a yellow solid (533 mg, yield 95%). ESI MS: m/z 165 [M+H]+.

1. customPOCl3 was removed under reduced pressure
2. dissolutionThe residue was dissolved with DCM (40 mL)
3. additionThen aqueous Na2CO3 was added cautiously
4. customThen the organic phase was separated from the aqueous phase
5. extractionthe aqueous phase was extracted with EtOAc (4×15 mL)
6. washThe combined organic layers were washed with brine (100 mL)
7. dry with materialdried over anhydrous Na2SO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure