ChemicalBook CAS DataBase List 2-Chloro-6-hydroxyquinoline

2-Chloro-6-hydroxyquinoline synthesis

5synthesis methods

Product Name:2-Chloro-6-hydroxyquinoline
CAS Number:577967-89-6
Molecular formula:C9H6ClNO
Molecular Weight:179.6

13676-02-3
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577967-89-6
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Yield: 93%

Reaction Conditions:

with boron tribromide in dichloromethane at 0 - 20; for 15 h;

Steps:

General procedure: To a cooled solution of aryl methyl ether ( 1.0 equiv.) in DCM (10 mL) was added BBr₃ (5.0 equiv.) slowly. The resulting mixture was stirred at 0 C and then warmed gradually to room temperature, and. stirred at room temperature for 15 hrs. After the reaction was completed, the reaction was quenched with NaHCO₃ solution (50 mL) and extracted with DCM (4 × 10 mL). The combined organic layers were washed with H₂O (3 × 10 mL), dried (Na₂SO₄) and concentrated in vacuo to afford the expected phenols. 2-chloroquinolin-6-ol: DHK-6-71 was prepared using general procedure G. Reaction was performed on a 2 g scale. DHK-6-71 was isolated as yellow solid. (1.72 g. 93%).

References:

Eli Lilly and Company;Cashion, D.K;chen, G.;Kasi, D;kolb, C;liu, C;sinha, A;Szardenings, A.k;wang, E;yu, C;zhang, W;Gangadharmath, Umesh B;Walsh, J.C CN102985411, 2016, B Location in patent:Paragraph 0906-0908