N-(6-Fluoro-2-methylquinolin-5-yl)acetamide → N-(6-Fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-5-yl)acetamide

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Reaction Steps

In one liter of acetic acid were dissolved 95 g of 5-acetamido-6-fluoroquinaldine. To this mixture were added 10 g of five percent platinum on charcoal. The mixture was hydrogenated with hydrogen gas at 30 psi on a Paar apparatus for five hours. The amount of hydrogen used was 61 psi (verus 62 psi theoretical). The catalyst was removed by filtration, and the filtrate was concentrated to 250 ml and decanted into cold stirred sodium hydroxide solution. The white precipitate was separated by filtration and triturated with a chloroform/hexane (50/50) mixture to provide white crystals of 5-acetamido-6-fluorotetrahydroquinaldine, m.p. 168°-170° C. The structural assignment was confirmed by infrared spectral analysis.

Provenance & Evidence