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ChemicalBook CAS DataBase List QUINMERAC
90717-03-6

QUINMERAC synthesis

4synthesis methods
Quinmerac is commercially produced through a multi-step synthesis starting with the Skraup reaction of 3-amino-4-chlorobenzoic acid with glycerol and sulfuric acid to form 8-chloroquinoline-3-carboxylic acid, followed by selective nucleophilic substitution of the 8-chloro group with methanethiol under basic conditions to yield 8-(methylthio)quinoline-3-carboxylic acid, which is then oxidised with hydrogen peroxide or peracid to the corresponding methylsulfonyl derivative, quinmerac.
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Yield:90717-03-6 96%

Reaction Conditions:

with manganese dioxide;nitric acid in sulfuric acid

Steps:

2 Preparation of 7-chloro-3-methylquinoline-8-carboxylic acid
Preparation of 7-chloro-3-methylquinoline-8-carboxylic acid 270.5 g of 8-bromomethyl-7-chloro-3-methylquinoline are dissolved in 950 g of 70% strength sulfuric acid, the solution is heated to 90° C. and 4.5 g of manganese dioxide are added. Thereafter, 290 g of 65% strength nitric acid are added dropwise in the course of 5 hours. The mixture is left to stand for a further 2 hours, cooled and diluted to twice the volume with water. The pH is brought to 3 with concentrated sodium hydroxide solution, and the precipitate is filtered off. The moist filter cake is boiled up with the same amount of methanol or isopropyl alcohol, and the mixture is filtered at 40° C. The acid thus obtained has a purity of 95%, and the yield is 96%.

References:

BASF Aktiengesellschaft US4845226, 1989, A

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