3-Bromoquinoline

3-Bromoquinoline reacts with mixed acids to form 3-bromo-5-nitroquinoline, which is then oxidized to 5-bromo-2,3-pyridinedicarboxylic acid upon heating with potassium permanganate. 6-Bromoquinoline reacts with nitric acid upon heating to form 6-bromo-8-nitroquinoline, which is then oxidized to 2,3-pyridinedicarboxylic acid upon reaction with potassium permanganate. 2-Bromoquinoline is prepared by reacting 2-hydroxyquinoline with phosphorus pentabromide. 3-Bromoquinoline is prepared by heating quinoline perbromide at 180°C. 4-Bromoquinoline is prepared by heating 4-hydroxyquinoline with phosphorus pentabromide, or by diazotizing 4-aminoquinoline. 5-Bromoquinoline is prepared by heating m-bromoaniline, glycerol, m-bromonitrobenzene, and concentrated sulfuric acid, or by diazotizing 5-aminoquinoline. 6-Bromoquinoline is prepared by heating p-bromoaniline with glycerol, concentrated sulfuric acid, and p-bromonitrobenzene. 7-Bromoquinoline is prepared by diazotization of 7-aminoquinoline. 8-Bromoquinoline is prepared by heating o-bromoaniline, glycerol, concentrated sulfuric acid, and o-bromonitrobenzene. Uses: As a reagent in organic synthesis.

There are seven position isomers with the main properties are as follows:

3-Bromoquinoline can have action with mixed acid to generate 3-bromo-5-nitroquinoline, followed by heating with potassium permanganate to be oxidized to 5-bromo-2, 3-pyridine dicarboxylic acid.
6-bromo-quinoline can be heated together nitric acid to generate 6-bromo-8-nitro-quinoline, followed by reaction with potassium permanganate to be oxidized into 2, 3-pyridinedicarboxylic acid.
2-bromo-quinoline can be manufactured through the reaction between 2-hydroxyquinoline and phosphorus pentabromide
3-bromo-quinoline can be obtained through heating the quinoline perbromide at 180 ° C.
4-bromoquinoline can be obtained through either the heating reaction between 4-hydroxyquinoline and phosphorus pentabromide or by the diazotization reaction of 4-aminoquinoline.
5-bromo-quinoline can be obtained from the heating reaction between m-bromo aniline, glycerol, m-bromonitrobenzene and concentrated sulfuric acid, or through the diazotization reaction of 5-amino-quinoline.
6-bromo-quinoline can be obtained through the heating reaction between p-bromoaniline, glycerol, concentrated sulfuric acid and p-bromo-nitrobenzene.
7-bromoquinoline can be obtained through the diazotization of 7-aminoquinoline.
8-bromo-quinoline can be obtained through the heating of o-bromo aniline, glycerol, concentrated sulfuric acid and o-bromo-nitrobenzene in the heating system.
Purposes: as organic synthesis reagents.

For pharmaceuticals
Medicine, pesticide intermediates

colorless to light yellow liquid

3-Bromoquinoline undergoes bromine-magnesium exchange reaction with lithium tributylmagnesate in toluene at -10°C, which is quenched by various electrophiles to yield functionalized quinolines.

The Journal of Organic Chemistry, 27, p. 1318, 1962 DOI: 10.1021/jo01051a047

3-Bromoquinoline undergoes bromine-magnesium exchange reaction with lithium tributylmagnesate in toluene at -10°C, which is quenched by various electrophiles to yield functionalized quinolines.

Not classified

[1] Patent: US3956301, 1976, A
[2] Patent: US5266700, 1993, A