Reaktion #161148

Reaktionsgleichung

Potassium nitrate

2-tert-butyl-phenylamine

→

2-tert-butyl-5-nitroaniline

Ausbeute 64.0%

Lösungsmittel

sulfuric acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with EtOAc three times
2. 2
   WaschenThe combined organic layers were washed with brine
3. 3
   Trocknendried over Na2SO4
4. 4
   SonstigeAfter removal of solvent
5. 5
   Sonstigethe residue was purified by recrystallization

Vorschrift

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+).

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