5,6,7,8-TETRAHYDROQUINOLIN-8-AMINE

A solution of 6, 7-dihydro-8(5H)-quinolinone oxime (0.50 g, 3.1 mmol, Synthetic Communications, 2003, 33, 3497-3502) in 35 ml_ of MeOH was subjected to catalytic hydrogenation at 50 psi in the presence of 50 mg of 10percent Pd on carbon. After 18 hours the reaction vessel was purged with nitrogen, catalyst removed by filtration through celite, and the filtrate concentrated to dryness at reduced pressure to afford 0.42 g (92percent) of 5, 6, 7, 8-tetrahydro-8-quinolinamine as a purple oil. To a solution of the azide (41.0 g, 0.256 mol) in methanol (250 mL) was added Pd/C (10percent, 4.1 g) and the mixture was hydrogenated at 30 psi on a Parr shaker. The mixture was filtered through celite and the cake was washed with methanol. The combined filtrates were evaporated and the residual oil was distilled (Kugelrohr, bp 115-140° C. @ 0.2 Torr) to provide 26.8 g (71percent) of 8-amino-5, 6, 7, 8-tetrahydroquinoline (AMD7488) as a pale yellow oil. Under stirring To a solution of 6, 7-dihydroquinoline-8(5H)-one (205 mg, 1.4 mmol) in 5 mL of saturated methanolic ammonia was added palladium on carbon (21 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere for 12 h. Filtered to remove palladium carbon, The filtrate is concentrated, Column chromatography of the residue gave the title compound as a red oil (189 mg, 92percent yield).A solution of 6, 7-dihydro-8(5H)-quinolinone oxime (0.50 g, 3.1 mmol, Synthetic Communications, 2003, 33, 3497-3502) in 35 ml_ of MeOH was subjected to catalytic hydrogenation at 50 psi in the presence of 50 mg of 10percent Pd on carbon. After 18 hours the reaction vessel was purged with nitrogen, catalyst removed by filtration through celite, and the filtrate concentrated to dryness at reduced pressure to afford 0.42 g (92percent) of 5, 6, 7, 8-tetrahydro-8-quinolinamine as a purple oil. 1H NMR (CDCI3): 5 8.39 (d, 1H), 7.36 (d, 1H), 7.04 (m, 1H), 4.00 (t, 1H), 2.88-2.67 (m, 2H), 2.18 (m, 1H), 2.03-1.62 (m, 5H).

Molecular Weight:148.20
XLogP3:0.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:148.100048391
Monoisotopic Mass:148.100048391
Topological Polar Surface Area:38.9
Heavy Atom Count:11
Complexity:136
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes