Hydroquinone → 4-[2,2-Dimethyl-5-(4-methylphenyl)-3,4-dihydro-2H-pyrrol-3-yl]pyridine

Participants

Reaction Steps

16 G. of 3-(p-methylphenyl)-2,2-dimethyl-2H-azirine and 26 g. of freshly distilled 4-vinylpyridine are irradiated in 2 l. of absolute benzene for 6 hours under the conditions given in Example 11 with the addition of 0.05 g. of p-hydroquinone. After evaporation of the solution under reduced pressure there remains a brown oil from which the excess 4-vinylpyridine is distilled off at 41°-42° C. and 0.01 Torr. The residue is taken up in a small amount of acetone. The crude crystallizate obtained from the acetone solution is chromatographed withe benzene/acetone (95:5) on silica gel. The combined fractions are evaporated to dryness under reduced pressure. Then, the residue is recrystallized twice with n-hexane, the solution which results is then decolorized with active carbon to yield 4-[2-(p-methylphenyl)-5,5-dimethyl-1-pyrrolin-4-yl]-pyridine with a melting point of 102° C.

Provenance & Evidence