4-aminonicotinic acid CAS number is 7418-65-7, chemical name is 4-aminopyridine-3-carboxylic acid, which is present in many natural product structures, is an important pharmaceutical intermediate, mainly used in the synthesis of cardiovascular and cerebrovascular diseases treatment. Its derivatives are analogs of the coenzyme nicotinamide adenine dinucleotide, which plays an important proton transfer role in cellular metabolism. its synthesis methods generally have three types:
The first one is using 3-methylpyridine as a starting material to oxidize to form pyridine nitrogen oxides, and then introduces C(4) amino groups by nitration and reduction. After amino protection, potassium permanganate oxidizes C(3) methyl group. The amino group is deprotected and the 4-aminonicotinic acid cas 7418-65-7 is obtained through a six-step reaction. The key intermediate of the method, pyridinium oxynitride has explosive properties and is unsafe to operate. The C(3) methyl potassium permanganate oxidation and the nitro iron powder reduction yield are not high, and the post-reaction treatment is cumbersome. The protection and deprotection of the C(4) amino group inevitably leads to a long synthesis route.
Secondly, The six nucleophilic addition of the active methylene compound and the nitropyrimidone was used to form a bridged ring structure, followed by elimination to obtain 4-aminonicotinic acid. However, the preparation of p-nitropyrimidinone requires a multi-step reaction such as 2-thiouracil reduction, methylation, and nitration. Nitrification will inevitably have some potential safety risks, and product purification requires column chromatography.
Thirdly, oxidative ring opening with isoquinoline as a raw material to produce a pale yellow solid 3,4-pyridinedicarboxylic acid. Intramolecular dehydration of 3,4-pyridinedicarboxylic acid under the action of acetic anhydride gave a pale yellow powder of 3,4-pyridinedicarboxylic anhydride, considering the positive charge of C(4)carbonyl carbon atom of 3,4-pyridinedicarboxylic anhydride is more higher, it is more susceptible to nucleophilic attack, regioselective aminolysis, ring opening to form 4-(aminocarbonyl)-3-pyridinecarboxylic acid, and finally introduce of C(4) amino group by Hofmann rearrangement to obtain the target product 4-aminonicotinic acid 7418-65-7.
Thera. Category:Organic Compound
Cas No.: 7418-65-7
Synonym:RARECHEM AL BE 1386;AURORA KA-2553;H-4ANIC-OH;IFLAB-BB F1957-0006;4-AMINO-3-CARBOXYPYRIDINE;4-AMINO-3-PYRIDINECARBOXYLIC ACID;4-AMINONICOTINIC ACID, 98.5%;4-AMINONICOTINIC ACID
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