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With hydrogenchloride; In 1,4-dioxane; water; for 18h;Reflux;
To a stirred solution of 2,4-dichloroquinoline (24.9 g, 126 mmol) in 1 ,4-dioxane (126 ml_) was added cone. HCI (83.8 ml_, 1.01 mol) dropwise. The reaction mixture was refluxed for 18h. The mixture was cooled to room temperature, poured into excess ice water and allowed to stir for 1 h. The precipitate was filtered and dried under vacuum to afford 4- chloroquinolin-2(1/-/)-one (19.2 g, 85%) as an off-white solid. LCMS (Method T2) RT 1.25 min; m/z 180.03 [M+H]+.
With hydrogenchloride; In 1,4-dioxane;Heating / reflux;
To a solution of optionally substituted 2,4-dichloroquinoline (10.0 mmol) in 1,4- dioxane (20 mL) was added HCl (6 N, 30 mL). The mixture was refluxed overnight. After cooling, 200 mL of water was added and precipitate was formed. The precipitate was collected and dried under vacuum. To the dry solid was added anhydrous acetone (50 mL), K2CO3 (2 equiv.) and MeI (5 equiv.). The mixture was heated to reflux overnight. The insoluble solid was filtered off and the solution was dried and purified on a column. The yields were around 50% for the two steps.
19.2 g
With hydrogenchloride; water; In 1,4-dioxane; for 19h;Reflux;
To a stirred solution of 2,4-dichloroquinoline (24.9 g, 126 mmol) in 1,4-dioxane (126 mL) was added conc. HCl (83.8 mL, 1.01 mol) drop-wise. The reaction mixture was refluxed for 18 h. The mixture was cooled to room temperature, poured into excess ice water and allowed to stir for 1 h. The precipitate was filtered and dried under vacuum to afford 4-chloro- 1 H-quinolin-2-one (19.2 g) as an off-white solid. LCMS (Method T2) Rt = 1.25 mins, mlz 180.03 [M+H]+.
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