2-Methylquinoline → Quinoline, 4-nitro-

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Reaction Steps

Using a similar reactor as in Synthesis Example 1, chinaldine (14.3 parts), 4-nitrophthalic acid (21.1 parts), zinc chloride (13.6 parts) and ODB (100 parts) were charged, followed by refluxing for 2 hours under stirring. The reaction mixture was filtered, and the filter cake was thoroughly washed with water and then dried to obtain 4-nitroquinoline. In a similar manner as in Synthesis Example 1, the 4-nitroquinoline was reduced for amination, followed by amidation with 2-bromoisobutyric acid bromide to obtain a 2-bromoisobutyric acid substitute. This will be called “Quinoline-1”. In a similar manner as in Synthesis Example 3, the structure of Quinoline-1 was confirmed by NMR and IR. By HPLC, its purity was determined to be 91.0%. By an elemental analysis, the bromine content was found to be 16.5%. A maximum absorption wavelength was measured by the spectrophotometer, and as a result, λmax=445 nm. The structural formula is shown below.

Provenance & Evidence