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Green Synthetic Methods for a Schiff Base from 2-Aminopyridine and 4-Ethoxybenzaldehyde
Journal of Applied Sciences and Environmental Management Pub Date : 2023-01-25 , DOI: 10.4314/jasem.v26i12.17
E. Ogbonda-Chukwu , O. J. Abayeh , O. Achugasim

The novel Schiff base was acquired from the reaction between 2-aminopyridine and 4-ethoxybenzaldehyde using three (3) techniques; refluxing in ethanol for 2 hours, stirring in ethanol and an ethanol-water (1:1) mixture at room temperature for an hour. The synthesis of the 2-aminopyridine-4-ethoxybenzaldehyde Schiff base produced dark yellow crystals with melting point range of 95-97oC. The reaction in ethanol under reflux produced the highest yield of 88.2% while the reaction in ethanol and ethanol-water (1:1 v/v) mixture at room temperature gave 69.2% and 43.5% yield of the compound respectively. The IR spectrum showed the following bands; 1681cm-1 (C=N), 1595cm-1 (aromatic C=C stretch), 2981cm-1 (aromatic C-H stretch), 1509cm-1 (aromatic C=N stretch), 1155cm-1 (aliphatic C-C stretch), 1036 (aromatic C-O stretch), 2825 (aliphatic C-H stretch). The 13C NMR spectrum showed the following chemical shifts (δppm); 158.48 (C=N, imino), 154.98 and 150.18 (C-N of aromatic pyridine moiety), 121.44 – 137.53 (aromatic carbons), 158.68 (aromatic C-O), 63.88 (aliphatic C-O), 15.22 (aliphatic C). The 1H NMR spectral data (δppm) for the compound gave the following results; 7.06-7.91, m (8H) (Ar-H), 9.71, s (1H) (HC=N-), 4.10, q (2H) and 1.32, t (3H) (OCH2CH3). The spectral data was in agreement to the predicted structure of the Schiff base.

中文翻译:

2-氨基吡啶和4-乙氧基苯甲醛席夫碱的绿色合成方法

使用三 (3) 技术从 2-氨基吡啶和 4-乙氧基苯甲醛之间的反应获得新型席夫碱;在乙醇中回流2小时,在乙醇和乙醇-水(1:1)混合物中于室温搅拌1小时。 2-氨基吡啶-4-乙氧基苯甲醛席夫碱的合成产生深黄色晶体,熔点范围为95-97oC。在乙醇中回流反应产生最高收率88.2%,而在乙醇和乙醇-水(1:1 v/v)混合物中在室温下反应分别产生69.2%和43.5%的化合物收率。红外光谱显示以下谱带; 1681cm-1 (C=N)、1595cm-1(芳香族 C=C 拉伸)、2981cm-1(芳香族 CH 拉伸)、1509cm-1(芳香族 C=N 拉伸)、1155cm-1(脂肪族 CC 拉伸)、1036 (芳香族 CO 拉伸),2825(脂肪族 CH 拉伸)。 13C NMR谱显示以下化学位移(δppm); 158.48(C=N,亚氨基)、154.98和150.18(芳香族吡啶部分的CN)、121.44 – 137.53(芳香族碳)、158.68(芳香族CO)、63.88(脂肪族CO)、15.22(脂肪族C)。该化合物的 1H NMR 光谱数据 (δppm) 给出以下结果: 7.06-7.91,m(8H)(Ar-H),9.71,s(1H)(HC=N-),4.10,q(2H)和1.32,t(3H)(OCH 2 CH 3 )。光谱数据与希夫碱的预测结构一致。
更新日期:2023-01-25
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