2-[1-(2-Chloro-4-nitrophenoxy)-1-methylethyl]pyridine → 3-Chloro-4-(1-methyl-1-pyridin-2-ylethoxy)aniline

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Reaction Steps

2-[1-(2-Chloro-4-nitrophenoxy)-1-methylethyl]pyridine (800 mg, 2.74 mmol) was dissolved in ethyl acetate (50 ml). The mixture was purged with nitrogen, and platinum on activated carbon (10%, 100 mg) was added. The mixture was hydrogenated for 6 hours using a burette filled with hydrogen. The system was degassed and purged with nitrogen, and the catalyst removed by filtration. The filtrate was concentrated in vacuo, and the residue purified by chromatography, eluting with 20% to 30% ethyl acetate in iso-hexane. The appropriate fractions were evaporated to give 3-chloro-4-(1-methyl-1-pyridin-2-ylethoxy)aniline as a straw-coloured oil (452 mg, 63%); NMR Spectrum (DMSO-d6, 400 MHz, CDCl3) 1.63 (s, 6H), 3.41 (bs, 2H), 6.25 (dd, 1H), 6.35 (d, 1H), 6.65 (d, 1H), 7.11 (ddd, 1H), 7.63 (ddd, 1H), 7.77 (d, 1H), 8.50 (d, 1H).

Provenance & Evidence