Nitric Acid → 4-(2-Methoxyethoxy)-2-nitroaniline

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

4-(2-Methoxyethoxy)aniline (500 mg) was added to acetic anhydride (2.38 g) and the mixture was cooled down to 10° C. HNO3 (65% in water, 0.62 mL) was added slowly in order to keep the temperature of the reaction mixture below 15° C. After the end of the addition, the reaction mixture was allowed to warm to RT over 1 h, was quenched with ice-cold water and stirred for 10 min. The resulting suspension was filtered off and dried in high vacuo. The resulting yellow powder was dissolved in dioxane (1.4 mL), treated with 6N HCl (1.4 mL) and the reaction mixture was stirred at 70° C. for 3 h. After cooling down to RT, water was added and the pH was adjusted to 10 with 1M NaOH. The layers were separated and the aq. phase was extracted with EA. The combined org. layers were washed with brine, dried (Na2SO4) and evaporated in vacuo to afford 303 mg of yellow solid. LC-MS (B): tR=0.99 min; [M+H]+: 213.05.

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