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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.
Picolinic acid is an organic compound with the formula NC 5 H 4 CO 2 H. It is a derivative of pyridine with a carboxylic acid (COOH) substituent at the 2-position. It is an isomer of nicotinic acid and isonicotinic acid , which have the carboxyl side chain at the 3- and 4-positions, respectively.
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)
The N-oxides of various pyridines are precursors to useful drugs: [9] Nicotinic acid N-oxide, derived from nicotinic acid is a precursor to niflumic acid and pranoprofen. 2,3,5-trimethylpyridine N-oxide is a precursor to the drug omeprazole; 2-chloropyridine N-oxide is a precursor to the fungicide zinc pyrithione
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 ...
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
The systematic name of this enzyme class is 2-amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioate carboxy-lyase (2-aminomuconate-semialdehyde-forming). Other names in common use include picolinic acid carboxylase, picolinic acid decarboxylase, alpha-amino-beta-carboxymuconate-epsilon-semialdehade decarboxylase, alpha-amino-beta-carboxymuconate-epsilon-semialdehyde, beta-decarboxylase, 2-amino-3-(3 ...