Acrylonitrile → Benzyltriethylammonium hydroxide
반응식
N[C:2]1[C:3]([N+]([O-])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.N[C:12]1C=N[CH:15]=[CH:16][C:17]=1[N+]([O-])=O.C(#N)[CH:22]=[CH2:23].O1CCO[CH2:27][CH2:26]1>>[OH-:9].[CH2:5]([N+:4]([CH2:22][CH3:23])([CH2:26][CH3:27])[CH2:3][CH3:2])[C:6]1[CH:7]=[CH:12][CH:17]=[CH:16][CH:15]=1참가 물질
5
실험 절차
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