Benzyl Bromide → 1-benzyl-4-hydroxy-1,6-naphthyridin-2(1H)-one

A mixture of methyl 4-(acetylamino)pyridine-3-carboxylate (70 g, 0.36 mol) and sodium hydride (50 g, 1.25 mol, 60% in mineral oil) in anhydrous tetrahydrofuran (800 mL) was stirred at room temperature for 30 minutes. To the above mixture was added bromomethylbenzene (60 g, 0.36 mmol) and the resulting mixture was stirred at room temperature overnight. The reaction mixture was poured onto crashed ice (600 mL), concentrated in vacuo, and washed with ethyl acetate (400 mL). The aqueous layer was neutralized by addition of 3 N aqueous solution of hydrochloric acid to pH 7. The formed solid was collected by filtration and dried in vacuo to afford 24 g of 1-benzyl-4-hydroxy-1,6-naphthyridin-2(1H)-one as a pale yellow solid.

1. stirringthe resulting mixture was stirred at room temperature overnight
2. additionThe reaction mixture was poured
3. concentrationconcentrated in vacuo
4. washwashed with ethyl acetate (400 mL)
5. additionThe aqueous layer was neutralized by addition of 3 N aqueous solution of hydrochloric acid to pH 7
6. filtrationThe formed solid was collected by filtration
7. customdried in vacuo

ORD-Eintrag

ord-2a01062b874d444296bd8dd27d24ff6f

Quelldatensatz

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08871756B2