ChemicalBook CAS DataBase List 3-Methoxyquinoline

3-Methoxyquinoline synthesis

12synthesis methods

Product Name:3-Methoxyquinoline
CAS Number:6931-17-5
Molecular formula:C10H9NO
Molecular Weight:159.18

5332-24-1
355 suppliers
$10.00/5g

124-41-4 Synthesis

124-41-4
681 suppliers
$12.00/25g

6931-17-5
74 suppliers
$16.00/100mg

Yield: 94%

Reaction Conditions:

with copper(l) iodide in N,N-dimethyl-formamide for 16 h;Reflux;Ullmann Condensation;

Steps:

4.1.3. 5-Bromo-3-methoxyquinoline (6)
Step 1: To a solution of 3-bromoquinoline (3) (6.5 mL, 48 mmol)in dimethylformamide (80 mL) were added sodium methanolate30% (16 mL, 54 mmol) and copper iodide (458 mg,2.4 mmol). The mixture was refluxed for 16 h, hydrolyzed andextracted with Et2O. The organic layer was washed with waterand brine, dried over MgSO4 and evaporated under vacuum toafford 3-methoxyquinoline in 94% yield as a colorless oil; 1HNMR (300 MHz, CDCl3) δ: 8.45 (d, 1H, 2.9 Hz), 7,85 (d, 1H, 8.1 Hzand 1.2 Hz), 7.49 (d, 1H, 8.1 Hz and 1.2 Hz), 7.36-7.25 (m, 2H),7.12 (d, 1H, 2.9 Hz), 3.67 (s, 3H); MS (APCI, pos. 30 V) m/z:[M+H]+, 160.

References:

Landagaray, Elodie;Ettaoussi, Mohamed;Rami, Marouan;Boutin, Jean A.;Caignard, Daniel-Henri;Delagrange, Philippe;Melnyk, Patricia;Berthelot, Pascal;Yous, Saïd [European Journal of Medicinal Chemistry,2017,vol. 127,p. 621 - 631]