반응 #676644

반응 방정식

NaHCO3

NaOAc

bromine

3-nitropyridin-4-amine

→

3-bromo-5-nitropyridin-4-amine

수율 77.0%

용매

acetic acid

water

반응 조건

후처리

1. 1
   workup.ADDITIONwas added to a sealed tube
2. 2
   기타consumption of starting material
3. 3
   농축The reaction mixture was concentrated
4. 4
   기타to obtain a solid which
5. 5
   추출extracted with EtOAc
6. 6
   기타The combined organic extracts were dried
7. 7
   농축concentrated

실험 절차

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).

출처