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6-BROMO-2(1H)-QUINOLONE, also known as halofantrine, is a synthetic chemical compound that is used as an antimalarial drug.
The production process of 6-bromo-2(1H)-quinolone involves several steps, which are outlined below.
Step 1: Preparation of the Starting Material
The production of 6-bromo-2(1H)-quinolone begins with the preparation of the starting material, which is a phenol derivative known as 2-chloro-1,4-benzenedicarboxylic acid.
This compound is synthesized by the reaction between benzene and chloral hydrate in the presence of an acid catalyst.
Step 2: Ring Closure Reaction
The next step in the production of 6-bromo-2(1H)-quinolone is the ring closure reaction, which involves the condensation of two molecules of 2-chloro-1,4-benzenedicarboxylic acid to form a benzoxazepine ring.
This reaction is carried out in the presence of a strong acid catalyst, such as sulfuric acid, and results in the formation of a substance known as diarylpropionate.
Step 3: Nitration
The diarylpropionate produced in the previous step is then nitrated using nitric acid to form a substance known as diarylpropionyl nitrate.
The nitration reaction is carried out in the presence of a solvent, such as acetonitrile, to ensure that the reaction proceeds in a controlled manner.
Step 4: Esterification
The next step in the production of 6-bromo-2(1H)-quinolone is the esterification of diarylpropionyl nitrate with a compound known as 2,2-dimethyl-4-oxo-1,3-oxazolidin-3-one.
This reaction is carried out in the presence of a catalyst, such as pyridine, and results in the formation of a substance known as diarylpropionyl 2,2-dimethyl-4-oxo-1,3-oxazolidin-3-one.
Step 5: Dehydration
The diarylpropionyl 2,2-dimethyl-4-oxo-1,3-oxazolidin-3-one produced in the previous step is then dehydrated using a dehydration agent, such as sulfuric acid.
This reaction results in the formation of a substance known as diarylpropionyl sulfate.
Step 6: Halogenation
The diarylpropionyl sulfate produced in the previous step is then treated with a halogenating agent, such as chlorine gas or hydrogen chloride.
This reaction results in the substitution of the sulfur atom in diarylpropionyl sulfate with a chlorine atom, resulting in the formation of a substance known as 6-chloro-2(1H)-quinolone.
Step 7: Reduction
The 6-chloro-2(1H)-quinolone produced in the previous step is then reduced using a reducing agent, such as lithium aluminum hydride, to form a substance known as 6-bromo-2(1H)-quinolone.
This reaction results in the substitution of the chlorine atom in 6-chloro-2(1H)-quinolone with a bromine atom.
The 6-bromo-2(1H)-quinolone produced in the previous step is then isolated and purified using a variety of techniques, such as crystallization, distillation, and chromatography.
The resulting pure 6-bromo-2(1H)-quinolone is then packaged