4-Nitroquinoline 1-Oxide → 2-Bromo-4-nitroquinoline

Temperatur

0 °C

4-Nitroquinoline 1-oxide (940 mg, 4.9 mmol) in chloroform (12 mL) was cooled to 0° C. To this solution, POBr3 (1.77 g, 6.2 mmol) was added in small portions. The mixture was stirred at 0° C. for 2 h and diluted with DCM (50 mL), and poured on ice (50 g). To this suspension, 1 M NaOH was added to adjust pH to about 9. Layers were separated and the organic layer was washed with water (2×50 mL) and dried over MgSO4 and concentrated. The crude product was purified by silica chromatography to afford 2-bromo-4-nitroquinoline as a yellow solid (620 mg, 50%). 1H NMR (400 MHz, CDCl3): δ 7.63-7.94 (m, 2H), 8.06 (s, 1H), 8.17 (t, J=7.16, 6.84 Hz, 1H), 8.38 (d, J=8.76 Hz, 1H).

1. additionpoured on ice (50 g)
2. customLayers were separated
3. washthe organic layer was washed with water (2×50 mL)
4. dry with materialdried over MgSO4
5. concentrationconcentrated
6. customThe crude product was purified by silica chromatography

ORD-Eintrag

ord-4d8e60cbe893472696bbbdd389219418

Quelldatensatz

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08491869B2