1,4-Dihydroxy-2,2,6,6-tetramethylpiperidine → 1-(2-Nitro-4-chlorophenoxy)-2,2,6,6-tetramethyl-4-hydroxypiperidine

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Reaction Steps

The procedure of Example 1 is repeated using 4.31 g (25 mmol) of 1-oxyl-2,2,6,6-tetramethyl-4-hydroxypiperidine, 7.73 g (75 mmol) of tert-butyl nitrite, 25 mg (0.25 mmol) of copper(II) flouride, 70 mL of pyridine and 5.61 g (32.5 mmol) of 4-chloro-2-nitroaniline at 70° C. The crude product obtained is purified by vacuum flash chromatography (70:30/heptane:ethyl acetate) to give 4.28 g of the title compound in 84.8% yield as a light yellow solid melting at 124-125.5° C. The structure is confirmed by 1Hnmr and elemental analysis.

Provenance & Evidence