6-Methyl-8-quinolinamine synthesis
- Product Name:6-Methyl-8-quinolinamine
- CAS Number:68420-93-9
- Molecular formula:C10H10N2
- Molecular Weight:158.2
68420-92-8
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Yield:68420-93-9 95%
Reaction Conditions:
with 10% Pd/C;hydrogen in methanol at 20; for 5 h;
Steps:
6-Methylquinolin-8-amine(25)
To a solution of 6-methyl-8-nitroquinoline (500 mg, 2.65 mmol) in MeOH (10 mL) was added 10% Pd-C (50 mg) and stirred under hydrogen balloon condition at rt for 5 h. The Pd-C was filtrated out through a pad of celite and washed with methanol. The filtrate was concentrated under vacuum. The crude was purified by column chromatography to afford 25 (400 mg, 95%); 1H NMR (300 MHz, DMSO-d6): δ 8.63 (dd, J = 4.1, 1.7 Hz, 1H), 8.06 (dd, J = 8.3, 1.5 Hz, 1H), 7.40 (dd, J = 8.3, 4.1 Hz, 1H), 6.84 (s, 1H), 6.71 (d, J = 1.7 Hz, 1H), 5.83 (s, 2H), 2.35 (s, 3H); LCMS (m/z) = 159 [M+1].
References:
Kannan, Murugan;Raichurkar, Anandkumar V.;Khan, Fazlur Rahman Nawaz;Iyer, Pravin S. [Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,# 5,p. 1100 - 1103] Location in patent:supporting information
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