The Synthetic Routes of 5-AMino-6-broMoisoquinoline

5-Amino-6-broMoisoquinoline is an important chemical intermediate that is used in the production of various pharmaceuticals, agrochemicals, and other chemical products.
The chemical structure of 5-amino-6-broMoisoquinoline is shown below:

Synthetic routes to 5-amino-6-broMoisoquinoline include several methods that are widely used in the chemical industry.

1. Hydrogenation of N-benzyloxy-N-methyl-6-bromo-1,2,3,4-tetrahydroquinoline

The first synthetic route to 5-amino-6-broMoisoquinoline involves the hydrogenation of N-benzyloxy-N-methyl-6-bromo-1,2,3,4-tetrahydroquinoline.
This starting material is easily prepared by the reaction of 6-bromo-1,2,3,4-tetrahydroquinoline with benzyl bromide and sodium hydroxide, followed by a hydrogenation step using a hydrogenation catalyst such as palladium on barium oxide.
The hydrogenation step converts the N-benzyloxy group to an N-methyl group, and the resulting product is then treated with a base to convert it to the desired amino intermediate.

2. Reduction of N-[1-(dicyclohexylcarbamoyl)-4-(nitrophenyl)butyl]-6-bromo-1,2,3,4-tetrahydroquinoline

Another synthetic route to 5-amino-6-broMoisoquinoline involves the reduction of N-[1-(dicyclohexylcarbamoyl)-4-(nitrophenyl)butyl]-6-bromo-1,2,3,4-tetrahydroquinoline.
This intermediate is prepared by the reaction of 6-bromo-1,2,3,4-tetrahydroquinoline with 1-(dicyclohexylcarbamoyl)-4-nitrobenzene in the presence of a base such as sodium hydroxide.
The resulting product is then reduced using a reducing agent such as lithium aluminum hydride to produce the desired amino intermediate.

3. Reduction of N-[1-(4-nitrophenyl)cyclohexyl]-6-bromo-1,2,3,4-tetrahydroquinoline

N-[1-(4-nitrophenyl)cyclohexyl]-6-bromo-1,2,3,4-tetrahydroquinoline is another intermediate that can be used to synthesize 5-amino-6-broMoisoquinoline.
This intermediate is prepared by the reaction of 6-bromo-1,2,3,4-tetrahydroquinoline with 4-nitrophenylcyclohexane in the presence of a base such as sodium hydroxide.
The resulting product is then reduced using a reducing agent such as lithium aluminum hydride to produce the desired amino intermediate.

4. Reduction of N-[1-(3-nitrophenyl)-2-(2-nitrophenyl)ethyl]-6-bromo-1,2,3,4-tetrahydroquinoline

N-[1-(3-nitrophenyl)-2-(2-nitrophenyl)ethyl]-6-bromo-1,2,3,4-tetrahydroquinoline is a synthetic intermediate that can be converted to 5-amino-6-broMoisoquinoline using a similar reduction process as described above.
This intermediate is prepared by the reaction of 6-bromo-1,2,3,4-tetrahydroquinoline with 2-nitrophenyl acetate and 3-nitrophenyl