2-Aminonicotinic acid CAS number is 5345-47-1, which is an important starting material for the synthesis of antibacterial and anti-inflammatory drugs naphthyridinone. There are three main synthetic methods: the first one uses 3-cyanopyridine or 3-guanidinium pyridine or nicotinic acid as a raw material to activate the pyridine ring by nitrogen oxidation, chlorination at the 2-position of the pyridine ring, hydroxylation, etc. Finally, 2-aminopyridine-3-carboxylic acid is obtained. Secondly, the synthesis of 2-aminonicotinic acid using pyridine N-oxide as an intermediate has disadvantages such as high cost of raw materials, difficulty in chlorination, and the like, and low yield. The above two methods have certain defects, and the third method has strong operability and is suitable for industrialized scale production. The approximate production process is as follows:
1. The catalyst S-SnO2/MWCNTs and 2,3-pyridinedicarboxylic acid and acetic anhydride are added to the reaction flask, and the reaction is heated for 4 hours, concentrated under reduced pressure, and the residue is dried to obtain a yellow mixed powder;
2, the above yellow mixed powder and a concentration of 28% aqueous ammonia was added to a round bottom flask with a condensing device, heated to 50℃ and stirred for 3 h;
3. After the reaction is completed, the pH is adjusted with hydrochloric acid, and a solid precipitates, and the filter cake is washed with distilled water until the filtrate is colorless, and dried under vacuum to obtain 2-amidepyridine-3-carboxylic acid;
4, adding 5mol·L-1 sodium hydroxide solution to the flask, adding bromine at 5℃, stirring for 0.5 h, adding 2-amide pyridine-3-carboxylic acid, heating to 85℃for 2 h;
5. After the reaction, a part of the solvent was concentrated under reduced pressure, cooled, adjusted to pH=7 with hydrochloric acid, filtered, filtered, dried, and then recrystallized from distilled water to give a white solid 2-Aminonicotinic acid CAS number 5345-47-1. The advantage of this method is that the intramolecular dehydration by 2,3-pyridinedicarboxylic acid and acetic anhydride gives 2,3-pyridinedicarboxylic anhydride. Due to the low density of electron cloud of carbonyl carbon atom of 2,3-pyridinedicarboxylic acid anhydride, it is more susceptible to nucleophilic attack, and regioselective aminolysis is opened to form 2-carbamoyl nicotinic acid, and finally ammonia is introduced by Hofmann degradation. Synthesis of the target molecule 2-aminonicotinic acid. In order to further improve the active site utilization rate of the catalyst system, the coating of SnO2 into a solid super acid S-SnO2 by ammonium acetate solution washing and sulfuric acid sulfonation not only improves the stability of the system, but also increases the catalytic activity of the catalyst. The raw material of the route is cheap and easy to obtain, the operation is safe, the product is separated and purified simply, and the target product has high yield.
Thera. Category:Organic Compound
Cas No.: 5345-47-1
Synonym:2-Aminopyridin-3-carboxylic acid for synthesis;2-AMINO-3-PYRIDINECARBOXYLIC ACID;MOLT-4 Cell;NSC 3049;2-AMino-3-carboxypyridine;Nicotinic acid, 2-aMino- (6CI,7CI,8CI);2-Aminopyridine-3-carboxylic acid, 2-Amino-3-carboxypyridine;2- aMinoacid;
Molecular Weight: 138.12
Molecular formula: C6H6N2O2
Assay: ≥98.%
Appearance: White Crystalline solid
Packing:Export worthy packing
Material Safety Data Sheet:Available on request
Usage:
intermedates:
6-Aminonicotinic acid CAS 3167-49-5
4-aminonicotinic acid CAS number is 7418-65-7
4-Aminonicotinic acid methyl ester CAS number is 16135-36-7
Methyl 6-Aminonicotinate CAS 36052-24-1
2-Aminonicotinic acid CAS number is 5345-47-1