Bromine → 4-Amino-3-bromo-5-nitropyridine

Temperatur

100 °C

A mixture of 3-nitropyridin-4-amine (LXVIII) (10 g, 71.94 mmol) and acetic acid (120 mL) was added to a sealed tube followed by addition of NaOAc (29.50 g, 93.52 mmol) and dropwise addition of bromine (4.7 ml 359.7 mmol) under stirring. The sealed tube was heated at 100° C. for 28 h until TLC showed consumption of starting material. The reaction mixture was concentrated to obtain a solid which was dissolved in water, basified with NaHCO3 and extracted with EtOAc. The combined organic extracts were dried and concentrated to produce 3-bromo-5-nitropyridin-4-amine (LXIX) as a yellow solid (12 g, 55 mmol, 77% yield). 1H NMR (DMSO-d6) δ ppm 9.19 (s, 1H), 8.58 (s, 1H); ESIMS found for C5H4BrN3O2 m/z 217, 219 (M+, M+2).

1. additionwas added to a sealed tube
2. customconsumption of starting material
3. concentrationThe reaction mixture was concentrated
4. customto obtain a solid which
5. extractionextracted with EtOAc
6. customThe combined organic extracts were dried
7. concentrationconcentrated

ORD-Eintrag

ord-93ccb0d0597343c78f29cc3aa9618c6b

Quelldatensatz

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08883822B2