Aniline → N-Ethylaniline

Temperature

0 °C

To a solution of aniline 22 (386 mg, 0.474 mmol, 1.0 eq.) in DMPU (1.6 mL) at 0° C. was added lithium hexamethyldisalazide (0.950 mL, 0.950 mmol, 2.0 eq., lithium hexamethyldisalazide 1.0 M in THF). The resulting mixture was stirred at 0° C. during 30 min and added ethyl iodide (0.230 mL, 2.88 mmol, 6.1 eq.). The reaction mixture was stirred 10 min at 0° C., then allowed to warm up to rt and stirred at that temperature during 1 h. A saturated solution of NH4Cl, methyl-t-butyl ether and n-hexanes were added. Layers were separated and the aqueous one was extracted twice with methyl-t-butyl ether/hexane (1:1 mixture). The combined organic layers were washed with brine/water (1:1 mixture), then with brine, dried with sodium sulfate, filtered and concentrated to dryness. The resulting foam was purified by chromatography on silica gel 230-400 Mesh using the following solvent gradient: 15% and 20% ethyl acetate/hexane to elute. This procedure afforded N-ethyl-aniline 39, 349 mg, white foam, 87% yield.

1. stirringThe reaction mixture was stirred 10 min at 0° C.
2. temperatureto warm up to rt
3. stirringstirred at that temperature during 1 h
4. customLayers were separated
5. extractionthe aqueous one was extracted twice with methyl-t-butyl ether/hexane (1:1 mixture)
6. washThe combined organic layers were washed with brine/water (1:1 mixture)
7. dry with materialwith brine, dried with sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated to dryness
10. customThe resulting foam was purified by chromatography on silica gel 230-400 Mesh
11. wash15% and 20% ethyl acetate/hexane to elute

ORD record

ord-5ff64cc54007421d922a25f856b6d3aa

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07799827B2