Reaktion #156104

Reaktionsgleichung

NaHCO3

NaOAc

bromine

3-nitropyridin-4-amine

→

3-bromo-5-nitropyridin-4-amine

Ausbeute 77.0%

Lösungsmittel

acetic acid

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added to a sealed tube
2. 2
   Sonstigeconsumption of starting material
3. 3
   EinengenThe reaction mixture was concentrated
4. 4
   Sonstigeto obtain a solid which
5. 5
   Extraktionextracted with ethyl acetate
6. 6
   SonstigeThe combined organic extracts were dried
7. 7
   Einengenconcentrated

Vorschrift

A mixture of 3-nitropyridin-4-amine (XII) (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 ethyl acetate. The combined organic extracts were dried and concentrated to produce 3-bromo-5-nitropyridin-4-amine (XIII) 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).

Quelle