4-Chloro-2-nitroaniline → 1-(2-Nitro-4-chlorophenoxy)-2,2,6,6-tetramethylpiperidine

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Reaction Steps

The procedure of Example 1 is repeated using 3.9 g (25 mmol) of 1-oxyl-2,2,6,6-tetramethylpiperidine, 7.84 g (76 mmol) of tert-butyl nitrite, 25 mg (0.25 mmol) of copper(II) fluoride, 120 mL of pyridine and 8.6 g (50 mmol) of 2-nitro-4-chloroaniline at 70° C. The crude product obtained is purified by vacuum flash chromatography (heptane) to give 5.2 g of the title compound as a light yellow oil in 66.7% yield. The structure is confirmed by 1Hnmr and mass spectroscopy analyses.

Provenance & Evidence