一种含吡啶环和三氟甲基取代基的芳香二胺的合成与表征

Synthesis and Characterization of a Novel Aromatic Diamine Bearing Pyridine Ring and Trifluoromethyl Substituent

以4-三氟甲基苯甲醛、4'-硝基苯乙酮和醋酸铵为原料,在冰醋酸介质中,通过改进的Chichibabin反应得到了二硝基化合物4-(4-三氟甲基苯基)-2,6-二(4-胺基苯基)吡啶(TMPBNPP),继而用Pd/C和水合肼将TMPBNPP进行还原,成功合成了一种新型含吡啶环和三氟甲基侧基的芳香二胺4-(4-三氟甲基苯基)-2,6-二(4-胺基苯基)吡啶(TMPBAPP),2步反应总收率为48%,并用核磁共振谱、红外光谱和X-射线衍射等手段对其结构进行了分析表征.

A novel aromatic diamine containing a pyridine heterocyclic ring and a trifluoromethyl substituent,4-（4-trifluoromethylphenyl）-2,6-bis（4-aminophenyl）pyridine（2） was successfully synthesized in by a modified Chichibabin reaction of 4-trifluoromethylbenzaldehyde,4′-nitroacetophenone and ammonium acetate in glacial acetic acid,followed by a reduction of the resulting dinitro compound,4-（4-trifluoromethylphenyl）-2,6-bis（4-aminophenyl）pyridine（1）with Pd/C and hydrazine monohydrate.The new diamine 2 was obtained in overall yield of about 48%（based on compound 4-trifluoromethylbenzaldehyde）.The structure of the target compound was characterized by 1H NMR,IR,elemental analysis and X-ray diffraction measurements.