2-(Dimethylamino)ethanol → [2-(5-Methoxy-2-nitrophenoxy)ethyl]dimethylamine

N,N-Dimethylethanolamine (0.80 g, 9.0 mmol) was added to a mixture of powdered KOH (0.50 g, 9.0 mmol) and Aliquat 336 (0.36 g, 0.9 mmol) and the resulting mixture was stirred for 5 minutes at 80° C. Then 2-fluoro-4-methoxy-1-nitrobenzene (1.28 g, 7.5 mmol) was added, and stirring proceeded at this temperature for 30 minutes. The mixture was cooled and partitioned between methylene chloride (80 mL) and dilute aqueous HCl (50 mL), and the organic layer was extracted with dilute aqueous HCl (2×50 mL). The combined aqueous phases were washed with methylene chloride (3×75 mL), basified (3N NaOH), and extracted with methylene chloride (3×75 mL). The combined organic extracts were washed with water (3×100 mL), dried (MgSO4), and evaporated, providing 1.3 g as a yellow oil, in 74% yield: 1H NMR (CDCl3) δ 2.36 (s, 6H), 2.81 (t, J=5.8 Hz, 2H), 3.86 (s, 3H), 4.17 (t, J=5.8 Hz, 2H), 6.47-6.54 (m, 2H), 6.97 (d, J=9.0 Hz, 1H).

1. stirringstirring
2. waitproceeded at this temperature for 30 minutes
3. temperatureThe mixture was cooled
4. custompartitioned between methylene chloride (80 mL) and dilute aqueous HCl (50 mL)
5. extractionthe organic layer was extracted with dilute aqueous HCl (2×50 mL)
6. washThe combined aqueous phases were washed with methylene chloride (3×75 mL)
7. extractionextracted with methylene chloride (3×75 mL)
8. washThe combined organic extracts were washed with water (3×100 mL)
9. dry with materialdried (MgSO4)
10. customevaporated
11. customproviding 1.3 g as a yellow oil

ORD-Eintrag

ord-e6c12130b1fb43f6a6e58bf370752ba5

Quelldatensatz

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08481568B2