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

577967-89-6

The general procedure for the synthesis of 2-chloro-6-hydroxyquinoline from 2-chloro-6-methoxyquinoline is as follows: General method: aryl methyl ether (1.0 eq.) was dissolved in dichloromethane (DCM, 10 mL) and cooled to 0 °C. Boron tribromide (BBr3, 5.0 eq.) was added slowly under stirring. The reaction mixture was stirred at 0 °C and then gradually warmed to room temperature and continued stirring at room temperature for 15 hours. Upon completion of the reaction, the reaction was quenched with sodium bicarbonate (NaHCO3) solution (50 mL) followed by extraction with DCM (4 x 10 mL). The organic layers were combined, washed with water (3 × 10 mL), dried over anhydrous sodium sulfate (Na2SO4), and finally concentrated under vacuum to obtain the target phenolic compounds. 2-Chloro-6-hydroxyquinoline (DHK-6-71) was prepared from 2 g scale of 2-chloro-6-methoxyquinoline using the above general method G. The product was a yellow solid in 93% (1.72 g) yield.

13676-02-3
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577967-89-6
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$15.00/250mg

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