Methyl Picolinimidate → 3-[2-(Pyridin-2-yl)-4,5-dihydro-1,3-oxazol-5-yl]phenol

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Reaction Steps

A mixture of (±) norphenylephrine hydrochloride (10 g, 0.05 mol) and methyl iminopicolinate (8 g, 0.059 mol) in tetrahydrofuran (300 ml) is heated to reflux for 16 hours. The mixture is dissolved in ethyl acetate and water. The aqueous layer is extracted twice with ethyl acetate. The combined ethyl acetate solutions are washed twice with dilute aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated to dryness to obtain a partially crystalline material. This material is triturated with ethyl ether to obtain crystals. These crystals are dissolved in hot acetonitrile and the hot solution is filtered and allowed to cool. The crystals (4 g) are filtered off, washed with acetonitrile and dried in vacuo, m.p. 139°-141° C.

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