Citric Acid Catalyzed Synthesis of Hydrazones Schiff Bases of 2,4-Dinirtophenyl Hydrazine

An efficient method for the Citric acid-catalyzed synthesis of hydrazones Schiff base using 2,4-dinirtophenyl hydrazine. We have synthesized a series of hydrazones using 2,4-dinirtophenyl hydrazine as a source of amine and substituted aromatic aldehydes and aromatic ketones as a carbonyl source. Synthesized compounds were characterized by FT-IR techniques. Synthesis of above hydrazones using citric acid as a catalyst proved to be a green and eco-friendly approach. Dinore J.M 1 , Yelwande A.A 1 , Palve M.P 1 , Sapkal A.V 2 1 IndraRaj Arts and Science College Sillod, DistAurangabad (M.S.) 431112, India. 2 Milind Arts and Science College Aurangabad (M.S.) 431004, India. Submission: 9 April 2016 Accepted: 12 April 2016 Published: 25 April 2016 www.ijppr.humanjournals.com Citation: Dinore J.M et al. Ijppr.Human, 2016; Vol. 6 (1): 349-354. 350 INTRODUCTION Compounds containing azomethine group (-CH=N-) are known as Schiff’s bases and they are synthesized by condensation of primary amine with carbonyl compounds (aldehydes & ketones). [1] Recently there has been considerable interest in the chemistry of hydrazine and hydrazone compounds because of their potential pharmacological applications. [2] Schiff base hydrazone compounds have been extensively used as versatile ligands in coordination chemistry and Schiff base hydrazone complexes are also very attractive model compounds for the elucidation of several biochemical processes. Hydrazones are used as intermediate in synthesis [3], as functional groups in metal carbonyls [4], in organic compounds [5, 6] and in particular hydrazone Schiff base ligands. [7-10] They also act as herbicides, insecticides, plant growth regulators and nematocides. [11-13] Hydrazones have been demonstrated to possess antimicrobial, anticonvulsant, analgesic, anti-inflammatory, anticancer activities. [14, 15] The chemistry of hydrazone derivatives has been investigated intensively in the last decade owing to their coordinative and pharmacological activity as well as their use analytical chemistry as metal extracting agents. [16, 17]The significance of Schiff bases like hydrazones lies in the fact that these compounds not only possess antimicrobial activities but also show greater tendency to form complexes. [18] In analytical chemistry hydrazones find applications as multidentate ligands for transition metals in colorimetric or fluorimetric determination. [19, 20] The above remarkable considerations, pharmaceutical and industrial applications encouraged us to synthesize hydrazone derivatives of 2, 4 dinitrophenyl hydrazine using Citric acid as a green catalyst. MATERIALS AND METHODS All chemicals were purchased either from S.D fine and Loba chemicals used without further purification. Melting points were taken in an open capillary and are uncorrected. FT-IR spectra were recorded on JASCO-FT-IR/4100, Japan, in KBr disc. All the reactions were carried out at room temperature. General procedure for the synthesis of Hydrazones Schiff bases A reaction mixture of 2,4-dinirtophenyl hydrazine (1 mmol), aromatic aldehydes/ketones (1 mmol) and citric acid (0.1 gm) in ethanol (15 ml) was stirred for specific time mentioned in www.ijppr.humanjournals.com Citation: Dinore J.M et al. Ijppr.Human, 2016; Vol. 6 (1): 349-354. 351 Table 3 at room temperature. Insoluble solid was gradually generated, then filter and wash with water. The crude product obtained was recrystallized from ethanol to afford pure products.