Glycerol → 1,7-Naphthyridin-8-amine

Temperatur

135 °C

A mixture of pyridine-2,3-diamine (5.0 g, 45.9 mmol), glycerol (21.1 g, 229 mmol), sodium 3-nitrobenzenesulphonate (20.6 g, 91.7 mmol), sulfuric acid (20 mL) and water (30 mL) was heated to 135° C. and stirred for 16 h. The mixture was cooled to room temperature and then poured into ice/water (150 g). The mixture was adjusted to pH ˜9 with saturated NaOH aqueous solution. Then the mixture was extracted with EtOAc (3×100 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduce pressure to give the crude product, which was purified by silica gel column (eluting with PE/EtOAc v/v 2:1) to give 1,7-naphthyridin-8-amine as a yellow solid (2.6 g, yield 39%). ESI MS: m/z 146.1 [M+H]+.

1. temperatureThe mixture was cooled to room temperature
2. extractionThen the mixture was extracted with EtOAc (3×100 mL)
3. dry with materialThe combined organic layers were dried over sodium sulfate
4. concentrationconcentrated
5. customto give the crude product, which
6. customwas purified by silica gel column (
7. washeluting with PE/EtOAc v/v 2:1)

ORD-Eintrag

ord-99e58f7230e347de97eac17f96437fd5

Quelldatensatz

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09249162B2