Hydrochloric Acid → Ethanamine, N-ethyl-2-(4-nitrophenoxy)-

Temperature

0 °C

2-(Ethylamino)-ethanol (2.5 g, 24.2 mmol) (Aldrich) was added to a cooled (−5° C.) mixture of sodium hydride (50%, 580 mg, 24.2 mmol) in dimethyl-formamide (100 mL) and stirred for 10 minutes at 0° C., 30 minutes at room temperature, then 30 minutes at 45° C. After cooling to −1° C., 1-fluoro-4-nitrobenzene (4.1 g, 29 mmol) (Aldrich) was added and the mixture was stirred 20 minutes at −100° C. and for 90 minutes at room temperature. The resulting mixture was adjusted to pH 2 with 6N hydrochloric acid and the mixture extracted with ether (4×50 mL). The aqueous layer was adjusted to pH 9 with 3N sodium hydroxide and extracted with ethyl acetate (5×50 mL), dried (Na2SO4), concentrated in vacuo, and dried under high vacuum at 40° C. to give 2.2 g (41%) ethyl-[2-(4-nitro-phenoxy)-ethyl]-amine.

1. temperaturea cooled
2. custom30 minutes
3. customat 45° C
4. temperatureAfter cooling to −1° C.
5. stirringthe mixture was stirred 20 minutes at −100° C. and for 90 minutes at room temperature
6. extractionthe mixture extracted with ether (4×50 mL)
7. extractionextracted with ethyl acetate (5×50 mL)
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated in vacuo
10. customdried under high vacuum at 40° C.

ORD record

ord-5d23b1cfe801444dbc28f2275f98ee8a

Source dataset

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06818663B2