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

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Reaction Conditions

Reaction Steps

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.

Provenance & Evidence