4-Nitrophenol → N,N-dimethyl-2-(4-nitrophenoxy)ethanamine

A mixture of 4-nitrophenol (3.5 g, 25 mmol), 2-(dimethylamino)ethyl chloride hydrochloride (3.6 g, 25 mmol), and potassium carbonate (13.2 g, 125 mmol) in acetone (100 mL) was heated to reflux for 30 hours. The solvent was removed under vacuum. The residue was partitioned between water (150 mL) and ethyl acetate (150 mL), and the aqueous phase was extracted with ethyl acetate (100 mL). The combined organic layers were washed with water (3×150 mL) and extracted with dilute aqueous HCl (2×125 mL). These extracts were washed with CH2Cl2 (2×150 mL), made basic (NaOH) and extracted into ethyl acetate (3×75 mL). These organic extracts were washed with water (3×75 mL), dried (MgSO4), and evaporated, providing 3.0 g as a pale yellow solid, in 57% yield; 1H NMR (CDCl3) δ 2.35 (s, 6H), 2.76 (t, J=5.6 Hz, 2H), 4.15 (t, J=5.6 Hz, 2H), 6.96-7.00 (m, 2H), 8.17-8.22 (m, 2H).

1. temperaturewas heated
2. temperatureto reflux for 30 hours
3. customThe solvent was removed under vacuum
4. customThe residue was partitioned between water (150 mL) and ethyl acetate (150 mL)
5. extractionthe aqueous phase was extracted with ethyl acetate (100 mL)
6. washThe combined organic layers were washed with water (3×150 mL)
7. extractionextracted with dilute aqueous HCl (2×125 mL)
8. washThese extracts were washed with CH2Cl2 (2×150 mL)
9. extractionextracted into ethyl acetate (3×75 mL)
10. washThese organic extracts were washed with water (3×75 mL)
11. dry with materialdried (MgSO4)
12. customevaporated
13. customproviding 3.0 g as a pale yellow solid

ORD record

ord-41d9ab5282104a719bedf9576b64753b

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08481568B2