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CAS No. : | 86129-62-6 | MDL No. : | MFCD24555889 |
Formula : | C9H10ClNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LCAOURNJLXCNNF-UHFFFAOYSA-N |
M.W : | 215.63 | Pubchem ID : | 57859986 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P270-P301+P312-P330-P501 | UN#: | |
Hazard Statements: | H302 | 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 |
---|---|---|
80% | In ethanol for 24h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With sodium hydroxide; hydrogen In ethanol for 1.75h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In 2-ethoxy-ethanol for 24h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With triethylamine In ethanol for 24h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 83 percent / triethylamine / ethanol / 24 h / Heating 2: 58 percent / various solvent(s) / 0.33 h / Heating 3: 25 percent / POCl3 / 3 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 80 percent / ethanol / 24 h / Heating 2: 1.) PCl5, POCl3, 2.) stannic chloride / 1.) reflux, 3 h, 2.) benzene, reflux, 1 h | ||
Multi-step reaction with 3 steps 1: 80 percent / ethanol / 24 h / Heating 2: 65 percent / polyphosphoric acid / 0.5 h / 120 °C 3: 14.8 percent / POCl3 / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 83 percent / triethylamine / ethanol / 24 h / Heating 2: 58 percent / various solvent(s) / 0.33 h / Heating 3: 5 percent / POCl3 / 3 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 80 percent / ethanol / 24 h / Heating 2: 65 percent / polyphosphoric acid / 0.5 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 83 percent / triethylamine / ethanol / 24 h / Heating 2: 58 percent / various solvent(s) / 0.33 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 80 percent / ethanol / 24 h / Heating 2: 1.) PCl5, POCl3, 2.) stannic chloride / 1.) reflux, 3 h, 2.) benzene, reflux, 1 h 3: 81.5 percent / ethanol / 2 h / Heating | ||
Multi-step reaction with 4 steps 1: 80 percent / ethanol / 24 h / Heating 2: 65 percent / polyphosphoric acid / 0.5 h / 120 °C 3: 14.8 percent / POCl3 / 2 h / Heating 4: 81.5 percent / ethanol / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 83 percent / triethylamine / ethanol / 24 h / Heating 2: 58 percent / various solvent(s) / 0.33 h / Heating 3: 25 percent / POCl3 / 3 h / Heating 4: 50 percent / 4 h / 140 °C / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 80 percent / ethanol / 24 h / Heating 2: 1.) PCl5, POCl3, 2.) stannic chloride / 1.) reflux, 3 h, 2.) benzene, reflux, 1 h 3: 79 percent / ethanol / 2 h / Heating | ||
Multi-step reaction with 4 steps 1: 80 percent / ethanol / 24 h / Heating 2: 65 percent / polyphosphoric acid / 0.5 h / 120 °C 3: 14.8 percent / POCl3 / 2 h / Heating 4: 79 percent / ethanol / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 83 percent / triethylamine / ethanol / 24 h / Heating 2: 58 percent / various solvent(s) / 0.33 h / Heating 3: 5 percent / POCl3 / 3 h / Heating 4: 78 percent / 2 h / 140 °C / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 80 percent / ethanol / 24 h / Heating 2: 1.) PCl5, POCl3, 2.) stannic chloride / 1.) reflux, 3 h, 2.) benzene, reflux, 1 h 3: 58 percent / ethanol / 2 h / Heating | ||
Multi-step reaction with 4 steps 1: 80 percent / ethanol / 24 h / Heating 2: 65 percent / polyphosphoric acid / 0.5 h / 120 °C 3: 14.8 percent / POCl3 / 2 h / Heating 4: 58 percent / ethanol / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | With sodium hydride In N,N-dimethyl acetamide; mineral oil at 20℃; for 15.5h; | 10 Ethyl 4-chloro-2-oxo-1-(2-oxo-2-phenylethyl)-1,2,5,6,7,8-hexahydroquinoline-3-carboxylate (6b) 5.10 Ethyl 4-chloro-6-methyl-2-oxo-1-(2-oxo-2-phenylethyl)-1,2-dihydropyridine-3-carboxylate (6c) In the same manner as in the preparation of 6a, the title compound (3.18 g, 23%) was obtained as a white powder from 5c (9.00 g, 41.7 mmol). 1H NMR (DMSO-d6) δ 1.25 (3H, t, J = 7.0 Hz), 2.30 (3H, s), 4.25 (2H, q, J = 7.0 Hz), 5.63 (2H, s), 6.54 (1H, d, J = 0.6 Hz), 7.61 (2H, t, J = 7.5 Hz), 7.72-7.78 (1H, m), 8.07-8.10 (2H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With triethylbutylammonium chloride; trichlorophosphate In acetonitrile at 40℃; for 1h; Reflux; | 57 Reference Example 57 Production of ethyl 4-chloro-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate A mixture of ethyl 4-hydroxy-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate (3.00 g, 15.2 mmol), phosphorus oxychloride (7.75 mL), n-butyltriethylammonium chloride (13.8 g, 60.8 mmol) and acetonitrile (60 mL) was stirred at 40°C for 30 min, and then for 30 min under refluxing conditions. After cooling, the reaction mixture was concentrated under reduced pressure, and water was added to the residue. The mixture was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was washed with a mixed solvent of ethyl acetate-hexane, and dried under reduced pressure to give the title compound (1.45 g, 44%) as a white powder. 1H NMR (300 MHz, DMSO-d6) δ:1.26 (3 H, t, J = 7.0 Hz), 2.20 (3 H, s), 4.25 (2 H, q, J = 7.0 Hz), 6.26 (1 H, s), 12.29 (1 H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With N-benzyl-N,N,N-triethylammonium chloride; trichlorophosphate In acetonitrile at 40℃; for 1h; Reflux; | 7 Ethyl 4-chloro-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylate (5b) 5.7 Ethyl 4-chloro-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate (5c) A mixture of 4c (3.00 g, 15.2 mmol), POCl3 (7.75 mL, 83.3 mmol), and benzyltriethylammonium chloride (13.8 g, 60.8 mmol) in MeCN (60 mL) was stirred at 40 °C for 30 min and at reflux for 30 min. After cooling, the reaction mixture was concentrated in vacuo, water was added to the residue, and the mixture was extracted with AcOEt. The extract was washed with brine, dried over MgSO4, and concentrated in vacuo. The residual solid was collected and washed with hexane/AcOEt to give the title compound (1.45 g, 44%) as a white powder. 1H NMR (DMSO-d6) δ 1.26 (3H, t, J = 7.0 Hz), 2.20 (3H, s), 4.25 (2H, q, J = 7.0 Hz), 6.26 (1H, s), 12.29 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl acetamide; mineral oil / 15.5 h / 20 °C 2: triethylamine / ethanol / 48 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium hydride / N,N-dimethyl acetamide; mineral oil / 15.5 h / 20 °C 2: triethylamine / ethanol / 48 h / Reflux 3: hydrogen; 10% Pd/C / methanol; tetrahydrofuran / 7 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: sodium hydride / N,N-dimethyl acetamide; mineral oil / 15.5 h / 20 °C 2: triethylamine / ethanol / 48 h / Reflux 3: hydrogen; 10% Pd/C / methanol; tetrahydrofuran / 7 h / 20 °C 4: sodium hydroxide / ethanol / 0.5 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl acetamide; mineral oil / 15.5 h / 20 °C 2.1: triethylamine / ethanol / 48 h / Reflux 3.1: hydrogen; 10% Pd/C / methanol; tetrahydrofuran / 7 h / 20 °C 4.1: sodium hydroxide / ethanol / 0.5 h / 60 °C 5.1: 1,2-dichloro-ethane; benzotriazol-1-ol / N,N-dimethyl-formamide / 15 h / 20 °C 5.2: 15 h / 20 °C |
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