Hydrochloric Acid → 1,5-Naphthyridin-3-amine

To a solution of 1.00 g of tert-butyl 1,5-naphthyridin-3-ylcarbamate in 6 mL of methanol, 1 mL of a 12 mol/L aqueous hydrogen chloride solution was added, and the mixture was stirred for 30 minutes. To the reaction mixture, 5 mL of methanol and 1 mL of a 12 mol/L aqueous hydrogen chloride solution were added, and the mixture was stirred at 40° C. for 40 minutes, and at 80° C. for 40 minutes. In the reaction mixture, the solvent was distilled off under reduced pressure, the mixture was neutralized with a saturated aqueous sodium hydrogen carbonate solution, and then the solvent was distilled off under reduced pressure. The resultant residue was washed with ethanol and, in the mother liquid, the solvent was distilled off under reduced pressure, and the resultant residue was purified with silica gel column chromatography using silica gel; Chromatorex-NH made by Fuji Silysia Chemical Ltd., and an eluent of chloroform:methanol=10:1 to obtain 0.50 g of 1,5-naphthyridin-3-amine as a yellow solid.

1. stirringthe mixture was stirred at 40° C. for 40 minutes
2. waitat 80° C. for 40 minutes
3. distillationIn the reaction mixture, the solvent was distilled off under reduced pressure
4. distillationthe solvent was distilled off under reduced pressure
5. washThe resultant residue was washed with ethanol and, in the mother liquid
6. distillationthe solvent was distilled off under reduced pressure
7. customthe resultant residue was purified with silica gel column chromatography

ORD record

ord-d3dd8ee8ba71497694f3b8b0521d691a

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08211908B2