반응 #161148

반응 방정식

Potassium nitrate

2-tert-butyl-phenylamine

→

2-tert-butyl-5-nitroaniline

수율 64.0%

용매

sulfuric acid

반응 조건

후처리

1. 1
   추출extracted with EtOAc three times
2. 2
   세척The combined organic layers were washed with brine
3. 3
   건조dried over Na2SO4
4. 4
   기타After removal of solvent
5. 5
   기타the residue was purified by recrystallization

실험 절차

To a cooled solution of sulfuric acid (90%, 50 mL) was added dropwise 2-tert-butyl-phenylamine (4.5 g, 30 mmol) at 0° C. Potassium nitrate (4.5 g, 45 mmol) was added in portions at 0° C. The reaction mixture was stirred at 0-5° C. for 5 min, poured into ice-water and then extracted with EtOAc three times. The combined organic layers were washed with brine and dried over Na2SO4. After removal of solvent, the residue was purified by recrystallization using 70% EtOH—H2O to give 2-tert-butyl-5-nitroaniline (3.7 g, 64%). 1H NMR (400 MHz, CDCl3) δ 7.56 (dd, J=8.7, 2.4 Hz, 1H), 7.48 (d, J=2.4 Hz, 1H), 7.36 (d, J=8.7 Hz, 1H), 4.17 (s, 2H), 1.46 (s, 9H); HPLC ret. time 3.27 min, 10-99% CH3CN, 5 min run; ESI-MS 195.3 m/z (MH+).

출처