7-Methoxy-4-quinolinol synthesis

6synthesis methods

Product Name:7-Methoxy-4-quinolinol
CAS Number:82121-05-9
Molecular formula:C10H9NO2
Molecular Weight:175.18

28027-17-0 Synthesis

4-HYDROXY-7-METHOXYQUINOLINE-3-CARBOXYLIC ACID

28027-17-0
90 suppliers
$9.00/250mg

82121-05-9
170 suppliers
$58.00/5g

Yield:82121-05-9 91%

Reaction Conditions:

in diphenylether; for 1 h;Reflux;

Steps:

7-Methoxyquinolin-4-ol (6i)

5i (4.90 g, 22.40 mmol) was added slowly to already boiling phenyl ether and allowed to reflux at 260°C for an hour. After cooling to room temperature the solid was filtered, washed with petroleum ether and dried. 6i (3.60 g, 91%) was obtained as a brown powdery solid, mp 209-211 °C (lit. Lauer et al 1946, 215 °C).³ δ_H (400 MHz; DMSO) 3.83 (3H, s, OCH₃), 5.92 (1H, d, J 7.4, H-3), 6.89 (1H, dd, J 2.3, 8.9 Hz, H-6), 6.97 (1H, d, J 2.0 Hz, H-8), 7.77 (1H, d, J 7.2 Hz, H-2), 7.97 (1H, d, J 8.9 Hz, H-5), 11.74 (1H, br s, Ar-OH). δ_C (100 MHz; DMSO) 55.9 (Ar-OCH₃), 99.8 (C-8), 109.0 (C-3), 113.4 (C-4a), 120.8 (C-6), 127.2 (C-5), 139.4 (C-8a), 142.4 (C-2), 162.3 (C-7), 176.9 (C-4).

References:

Nsumiwa, Samkele;Kuter, David;Wittlin, Sergio;Chibale, Kelly;Egan, Timothy J. [Bioorganic and Medicinal Chemistry,2013,vol. 21,# 13,p. 3738 - 3748] Location in patent:supporting information