Reacción #676641

Ecuación de reacción

NaHCO3

NaOAc

bromine

3-nitropyridin-4-amine

→

3-bromo-5-nitropyridin-4-amine

Rendimiento 87.4%

Disolventes

acetic acid

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added to a sealed tube
2. 2
   ConcentraciónThe reaction mixture was concentrated under vacuum
3. 3
   Otroto obtain a solid which
4. 4
   Extracciónextracted with DCM
5. 5
   OtroThe combined organic extracts were dried
6. 6
   Concentraciónconcentrated

Procedimiento

A mixture of 3-nitropyridin-4-amine (LXVIII) (10 g, 71.88 mmol) and acetic acid (100 ml) was added to a sealed tube followed by addition of NaOAc (29.50 g, 359 mmol) and dropwise addition of bromine (4.43 ml 86.3 mmol) under stirring. The sealed tube was heated at 100° C. for overnight. The reaction mixture was concentrated under vacuum to obtain a solid which was dissolved in water, basified with saturated aqueous NaHCO3 and extracted with DCM. The combined organic extracts were dried and concentrated to produce 3-bromo-5-nitropyridin-4-amine (LXIX) as a yellow solid (13.7 g, 62.8 mmol, 87% yield). 1H NMR (DMSO-d6, 500 MHz) δ ppm 8.58 (s, 1H), 9.19 (s, 1H); ESIMS found for C5H4BrN3O2 m/z 218.1 (M+H).

Fuente