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

Temperatur

10 °C

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.

1. customthe temperature of the reaction mixture below 15° C
2. additionAfter the end of the addition
3. temperatureto warm to RT over 1 h
4. customwas quenched with ice-cold water
5. filtrationThe resulting suspension was filtered off
6. customdried in high vacuo
7. dissolutionThe resulting yellow powder was dissolved in dioxane (1.4 mL)
8. additiontreated with 6N HCl (1.4 mL)
9. stirringthe reaction mixture was stirred at 70° C. for 3 h
10. temperatureAfter cooling down to RT
11. additionwater was added
12. customThe layers were separated
13. extractionthe aq. phase was extracted with EA
14. washlayers were washed with brine
15. dry with materialdried (Na2SO4)
16. customevaporated in vacuo

ORD-Eintrag

ord-92f57f6edfc74ceba8dd28fbe75b2929

Quelldatensatz

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09266876B2