5-methoxyquinolin-3-amine synthesis

Yield: 12%

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon in ethyl acetate at 20;

Steps:

20
0333] A mixture of 5- and 7-methoxy substituted 3-nitroquinolines (780 mg,3.82 mmol) was dissolved in EtOAc (75 mL) and the reaction mixture sparged with N₂ for several minutes. 10% Pd/C (54 mg) was then added and a H₂ balloon was connected to the reaction flask. The reaction mixture was sparged with H₂ and stirred at room 7 001708temperature under H₂ atmosphere overnight. Solvent removal in vacuo and purification by column chromatography on silicagel (100% EtOAc) afforded the two separated isomers 5-methoxyquinolin-3-amine and 7-methoxyquinolin-3-amine. The desired product 5-methoxyquinolin-3-amine (80 mg, 12%) was obtained as a yellow powder. The structure was assigned by ¹H NMR (CD₃OD): δ 8.40 (d, IH), 7.69 (d, IH), 7.40 (d, IH), 7.30 (t, IH), 6.85 (d, IH). LC/MS (desired isomer) (m/z): 175.0 (MH⁺), R_t 1.54 minutes; LC/MS (undesred isomer) (m/z): 175.0 (MH⁺), Rt 1.53 minutes.

References:

NOVARTIS AG WO2007/84786, 2007, A1 Location in patent:Page/Page column 117-118