Metal Catalyst-Free Amination of 2-chloro-5-nitrobenzoic Acid in Superheated Water

Abstract

A series of N-arylanthranilic acid derivatives were synthesised by amination of 2-chloro-5-nitrobenzoic acid with various arylamine in superheated water with potassium carbonate as base. Good yields were achieved within 2−3 h at 150−190 °C. The results indicated that this metal catalyst-free method is a simple, environmentally-friendly and efficient synthesis of N-phenylanthranilic acid derivatives. Furthermore, it will work with an alkylamine and phenol.

Novel 6-Aminoquinazolinone Derivatives as Potential Cross GT1-4 HCV NS5B Inhibitors

“…The purity of the compounds was found to be more than 95%. Compounds 5-nitro-2-(phenylamino)-benzoic acid 1a [48], 5-nitro-2-(m-tolylamino)benzoic acid 1b [49], and 5-nitro-…”

“…The purity of the compounds was found to be more than 95%. Compounds 5-nitro-2-(phenylamino)-benzoic acid 1a [48], 5-nitro-2-(m-tolylamino)benzoic acid 1b [49], and 5-nitro-2-(phenylamino)benzamide 3a [50,51] were synthesized according to the reported procedures.…”

“…The synthetic strategies designed for the preparation of 5-nitro-2-(substituted phenylamino)benzamide derivatives 3a,b, 2-substituted phenoxy-N-(4-oxo-1-(substituted phenyl)-1,4-dihydro quinazolin-6-yl)acetamide derivatives 7a-f, and 2-substituted phenoxy-N-(2-methyl-4-oxo-1-(substitutedphenyl)-1,4-dihydroquinazolin-6-yl)acetamide 11a-f are illustrated in Schemes 1-3. The starting material 5-nitro-2-chlorobenzoic acid was fused with aromatic amines, namely, aniline and 3-methylaniline, at 120 • C to afford 5-nitro-2-(phenylamino)-benzoic acid 1a [48] and 5-nitro-2-(m-tolylamino)benzoic acid 1b [49], respectively. The formation of compounds 1a,b is believed to proceed via an S N Ar additionelimination reaction [48].…”

Synthesis, Structure and Fluorescence Properties of a Zn(II) Coordination Polymer Based on 2-(Hydroxymethyl)-1H-Imidazole-4,5-Dicarboxylate

“…N-heterocyclic carboxylic acids have been used widely in the preparation of coordination polymers as they contain O donors as well as N donors and can coordinate to metal ions with various coordination modes, which can lead to polymers with intriguing structures and interesting properties. [1][2][3] Until now, many polymers constructed from these kinds of ligands have been reported, including zero-, one-, two-and three-dimensional products, [4][5][6][7] but it is often difficult to predict the exact structures and compositions of the final products owing to the influence of many factors, such as the structural characterisation of the organic ligand, the coordination nature of the metal ion, the counter anion, the pH value, the solvent and the temperature. For example, solvothermal reaction of 2-(hydroxymethyl)-1H-imidazole-4,5-dicarboxylic acid (H 4 hmIDC) with BaCl 2 can give the coordination polymer [Ba 3 (µ 5 -H 2 hmIDC) (µ 5 -H 3 hmIDC)(µ 4 -NO 3 ) 2 (µ 3 -Cl)] n in DMF-CH 3 CN-HNO 3 solution, 8 or [Ba(µ 3 -H 3 hmIDC) 2 (µ 1 -H 2 O)] n in ethanol-water solution 9 or [Ba(µ 3 -H 3 hmIDC)(µ 4 -H 3 hmIDC)] n in ethanol-DMF solution.…”