Tetralin → 3-(N-Propionyl)amino-1,2,3,4-tetrahydroquinoline

Participants

Reaction Steps

To a solution of 17.4 g (86.9) 3-(N-propionyl)aminoquinoline and 20.0 g (317 mmol) ammonium formate in 150 ml methanol was added 1.0 g Pd/C cautiously under an inert atmosphere. After stirring at ambient temperature for 2 days the reaction stopped. The ratio between starting material and product was approximately 1:1 (monitored by GLC). The mixture was filtered on Celite and evaporated to a residue from which the product was extracted into diethyl ether. The ether solution was dried (magnesium sulfate), filtered and evaporated. The product/starting material mixture was then recharged in a similar manner using the same amounts of reactants. After additional 4 days the reaction was completed and worked-up as above to yield 9.7 g (55%) of reasonably pure material: MS m/e 204 (M+, 4), 130 (100), 131 (45), 118 (8), 91 (5), 77 (5).

Provenance & Evidence