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Picolinic acid is a bidentate chelating agent of elements such as chromium, zinc, manganese, copper, iron, and molybdenum in the human body. [5] [6] It is a substrate in the Mitsunobu reaction. In the Hammick reaction, picolinic acid reacts with ketones to give pyridine-2-carbonols: [7] NC 5 H 4 CO 2 H + R 2 C=O → NC 5 H 4 CR 2 (OH) + CO 2
Upon heating α-picolinic acid will spontaneously decarboxylate forming the so-called 'Hammick Intermediate' (3).This was initially thought to be an aromatic ylide, but is now believed to be a carbene [5] [6] In the presence of a strong electrophile, such as an aldehyde or ketone, this species will undergo nucleophilic attack faster than proton transfer.
A pyridinecarboxylic acid is any member of a group of organic compounds which are monocarboxylic derivatives of pyridine. Pyridinecarboxylic acid comes in three isomers: Picolinic acid (2-pyridinecarboxylic acid) Nicotinic acid (3-pyridinecarboxylic acid), also known as Niacin; Isonicotinic acid (4-pyridinecarboxylic acid)
Nicotinonitrile or 3-cyanopyridine is an organic compound with the formula NCC 5 H 4 N. The molecule consists of a pyridine ring with a nitrile group attached to the 3-position. A colorless solid, it is produced by ammoxidation of 3-methylpyridine: [2] H 3 CC 5 H 4 N + NH 3 + 1.5 O 2 → NCC 5 H 4 N + 3 H 2 O. Nicotinonitrile is a precursor to ...
He recognized the acid from β–picoline as Nicotinsäure (nicotinic acid or "niacin"), [12] which Weidel had discovered in 1873. [13] When Weidel decarboxylated the carboxylic acid of each isomer – by dry distilling its calcium salt with calcium oxide – the reaction yielded pyridine, thus showing that picoline was a mixture of three ...
Isonicotinic acid or pyridine-4-carboxylic acid is an organic compound with the formula C 5 H 4 N(CO 2 H). It is a derivative of pyridine with a carboxylic acid substituent at the 4-position. It is an isomer of picolinic acid and nicotinic acid, which have the carboxyl group at the 2- and 3-position respectively compared to the 4-position for ...
Chlorpyrifos is produced from 3,5,6-trichloro-2-pyridinol, which is generated from 3-picoline by way of cyanopyridine. This conversion involves the ammoxidation of 3-methylpyridine: CH 3 C 5 H 4 N + 1.5 O 2 + NH 3 → NCC 5 H 4 N + 3 H 2 O. 3-Cyanopyridine is also a precursor to 3-pyridinecarboxamide, [3] [4] [5] which is a precursor to ...
2-Picoline is also a precursor to the agrichemical, nitrapyrin, which prevents loss of ammonia from fertilizers. Oxidation by potassium permanganate affords picolinic acid: [1] Treatment of 2-methylpyridine with butyllithium results in deprotonation of the methyl group: [4] H 3 CC 5 H 4 N + BuLi → LiH 2 CC 5 H 4 N + BuH