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CAS No. : | 20146-59-2 | MDL No. : | MFCD00234492 |
Formula : | C9H6ClNO | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | YJXTZWWKNXVRHA-UHFFFAOYSA-N |
M.W : | 179.60 | Pubchem ID : | 298329 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H320-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With sulfuric acid; nitric acid; at 0℃; for 1h; | A mixture of 4-chloro-1/-/-quinolin-2-one (from step 1 ; 17.8 g, 98.9 mmol) in sulfuric acid (52.7 mL, 989 mmol) was cooled to 0 C. Nitric acid (70%) (9.9 mL, 109 mmol) was added dropwise. The solution was stirred at 0 C for 1 h and then poured onto ice water. The yellow precipitate that formed was filtered and washed with water, methanol, ethyl acetate and diethyl ether before being stirred under vacuum at 120 C for approx. 10 min affording 4-chloro-6-nitroquinolin-2(1/-/)-one (21.5 g, 97%) as a pale yellow solid. LCMS (Method T2) RT 1.27 min; m/z 225.01 [M+H]+. |
21.5 g | With sulfuric acid; nitric acid; at 0℃; for 1h; | A mixture of 4-chloro-1 H-quinolin-2-one (17.8 g, 98.9 mmol) in sulfuric acid (52.7 mL, 989 mmol) was cooled to 0 00. Nitric acid (70%) (9.90 mL, 109 mmol) was added dropwise. The solution was stirred at 0 00 for 1 h and then poured onto ice water. The yellow precipitate that formed was filtered and washed with water, methanol, ethyl acetate and diethyl ether before being stirred under vacuum at 120 00 for -10 mins affording 4-chloro-6-nitro-1H- quinolin-2-one (21.5 g) as a pale yellow solid. LCMS (Method T2) Rt = 1.27 mins, mlz 225.01 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | 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]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In acetone;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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water; potassium carbonate; p-toluenesulfonyl chloride; In chloroform; at 20℃; for 5h; | To 30 mL of a chloroform solution containing 910 mg of 4-chloroquinoline N-oxide, 1.21 g of p-toluenesulfonyl chloride and 10 mL of an aqueous solution containing 2.47 g of potassium carbonate were added, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was added with water, the organic layer was separated, the resultant solution was washed sequentially with water and an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [silica gel; Silica gel 60 manufactured by Kanto Chemical Co., Inc., eluent; chloroform : methanol = 4 : 1] to obtain 560 mg of a pale yellow solid, 4-chloroquinolin-2(1H)-one. 1H-NMR (CDCl3) delta: 6.88 (1H, s), 7.27-7.37 (1H, m), 7.38-7.45 (1H, m), 7.54-7.65 (1H, m), 7.97 (1H, dd, J=8.4, 1.3 Hz) |
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