Acrylonitrile → Benzyltriethylammonium hydroxide

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Reaction Steps

An aminonitropyridine derivative II, such as 3-amino4-nitropyridine, may be treated with a mixture of acrylonitrile and a suitable base such as Triton B (N-benzyltriethylammonium hydroxide) in an appropriate solvent such as dioxane at room temperature for 1-4 days to give the illustrated nitrile derivative III. Treatment of derivative III with a suitable reduction catalyst such as Pd/C in an appropriate solvent such as ethyl acetate under hydrogen atmosphere of about 50-60 psig for about 3-12 h gives the amino derivative IV. This derivative may be heated with ethyl ethoxycarbonylacetimidate hydrochloride in a suitable solvent such as EtOH for about 4-24 h to give the the ester V. Treatment of derivative V with an anhydrous acid such as HCl(g) in an appropriate solvent such as EtOH at reflux for 4-24 h gives the diester VI. This diester may be treated with a suitable base such as sodium ethoxide in an appropriate solvent such as EtOH for about 12-24 h at room temperature followed by treatment with ethanolic HCl to give the derivative

Provenance & Evidence