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CAS No. : | 911434-04-3 | MDL No. : | |
Formula : | C12H13BrN2O6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 361.15 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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 |
---|---|---|
96% | for 5 h; Heating / reflux | 5-Bromo-2-methyl-3-nitro-pyridine 2-(5-Bromo-3-nitro-pyridin-2-yl)-malonic acid diethyl ester (Intermediate 24) (12.6 g) was added to 7.0 N HCl (100 mL) and heated to reflux for 5 hours, the reaction was cooled, extracted with diethyl ether (3*250 mL), dried (MgSO4) and solvent removed in vacuo to yield a yellow oil. Purification by flash chromatography on silica using 20percent diethylether in iso-hexane as eluent gave the title compound as a yellow waxy solid (7.5 g, 96percent); 1H NMR (300.072 MHz, cdcl3) .box. 8.79 (s, 1H), 8.43 (s, 1H), 2.83 (s, 3H). |
95% | With hydrogenchloride In waterReflux | diethyl (5-bromo-3-nitropyridin-2-yl)propanedioate (6.8 g, 18.8 mmol) was refluxed in 290 ml of 6M HCl overnight. The reaction mixture was allowed to cool down to room temperature, and the mixture was neutralized with NaOH in an ice bath to pH 10. The solution was extracted with dichloromethane (DCM), dried, and evaporated to a yellow solid, 3.88 g, in 95percent yield. |
89.7% | for 5 h; Reflux | Step 2 - Synthesis of 5-bromo-2-methyl-3-nitropyridineA mixture of diethyl 2-(5-bromo-3-nitropyridin-2-yl)malonate (1.2 g, 3.3 mmol) was added to 7.0 N HCl (10 mL) and heated to refluxed for 5 hours, the reaction was cooled to room temperature and extracted with DCM : MeOH = 10 : 1, the organic phase was dried (Na2S04) and concentrated, the resulting residue was purified using column chromatography eluted with PE : EtOAc = 4 : 1 to provide 5-bromo-2-methyl-3-nitropyridine (0.7 g, yield:89.7percent).1H-NMR (CDC13, 400 MHz) δ 8.76 (s, 1H), 8.40 (s, 1H), 2.80 (s, 3H). |
89.7% | for 5 h; Reflux | Step 2 - Synthesis of 5-bromo-2-methyl-3-nitropyridine A mixture of diethyl 2-(5-bromo-3-nitropyridin-2-yl)malonate (1.2 g, 3.3 mmol) was added to 7.0 N HCl (10 mL) and heated to refluxed for 5 hours, the reaction was cooled to room temperature and extracted with DCM : MeOH = 10 : 1, the organic phase was dried (Na2S04) and concentrated, the resulting residue was purified using column chromatography eluted with PE : EtOAc = 4 : 1 to provide 5-bromo-2-methyl-3-nitropyridine (0.7 g, yield:89.7percent). 1H- MR (CDC13, 400 MHz) δ 8.76 (s, 1H), 8.40 (s, 1H), 2.80 (s, 3H). (M+H)+: 217 / 219. |
84% | With hydrogenchloride In water for 18 h; Reflux | Example 635-bromo-2-methyl-3-nitropyridineA stirred mixture of diethyl 2-(5-bromo-3-nitropyridin-2-yl)malonate (12.5 g, 34.6 mmol) in HCI (7 N in water, 200 ml.) is heated at reflux for 18 hours. The mixture is cooled to room temperature and extracted with CH2CI2 (3 x 200 ml_). Organic layer is collected, dried over Na2S04, filtered and concentrated to dryness. The crude product is purified viachromatography using CH2CI2 to afford the title compound (5.8 g, 84percent) as a yellow solid: Rf 0.67 (CH2CI2); LCMS (m/z) = 217.1 , 219.2 [M+H]+, fR = 2.01 min. |
83% | With hydrogenchloride In water for 3 h; Reflux | The title compound is prepared as described in WO 2006/103449 (intermediate 24).C-l (40.0 g, 111 mmol) is taken up in 110 mL IN HC1 and the reaction mixture is stirred under reflux for 3 h. After cooling to RT, the aqueous phase is extracted with DCM, the combined organic layers are washed with saturated aqueous NaHC03-solution, dried over MgS04, filtered, and the solvent is evaporated under reduced pressure. Yield: 20.0 g (83percent). |
83% | With hydrogenchloride In water for 3 h; Reflux | The title compound is prepared as described in WO 2006/103449 (intermediate 24).C-l (40.0 g, 111 mmol) is taken up in 110 mL IN HC1 and the reaction mixture is stirred under reflux for 3 h. After cooling to RT, the reaction mixture is extracted with DCM, the combined organic layers are washed with saturated aqueous NaHC03, dried over MgS04, filtered, and the solvent is removed under reduced pressure. Yield: 20.0 g (83percent). |
83% | With hydrogenchloride In water for 3 h; Reflux | The title compound is prepared as described in (intermediate 24). C-1 (40.0 g, 111 mmol) is taken up in 110 mL 1N HCl and the reaction mixture is stirred under reflux for 3 h. After cooling to RT, the reaction mixture is extracted with DCM, the combined organic layers are washed with saturated aqueous NaHCO3, dried over MgSO4, filtered, and the solvent is removed under reduced pressure. Yield: 20.0 g (83percent). |
83% | With hydrogenchloride In water for 3 h; Reflux | The title compound is prepared as described in WO 2006/103449 (intermediate 24). C-1 (40.0 g, 111 mmol) is taken up in 110 mL 1N HCl and the reaction mixture is stirred under reflux for 3 h. After cooling to RT, the aqueous phase is extracted with DCM, the combined organic layers are washed with saturated aqueous NaHCO3-solution, dried over MgSO4, filtered, and the solvent is evaporated under reduced pressure. Yield: 20.0 g (83percent). |
75% | at 105℃; | Step 2: 5-Bromo-2-methyl-3-nitropyridine; To diethyl (5-bromo-3-nitropyridin-2-yl)malonate (66 g, 0.18 mol) was added water (250 mL) and 12 M HCl (360 mL, 4.32 mol). The mixture was heated at 105 0C until TLC showed starting material was consumed. The reaction mixture was then allowed to cool to rt and brine (0.67 L) was added. The organic solution was separated and the aqueous solution was extracted with DCM (3 x 0.67L). The organic solutions were combined, washed with brine, sat. aq. NaHCO3, and brine again, dried over Na2SO4, filtered and concentrated to give 5-bromo-2-methyl-3-nitropyridine (34.7 g, 75percent) as a yellow solid. |
72% | Stage #1: for 18 h; Reflux Stage #2: With sodium hydrogencarbonate In water at 0℃; |
A mixture of the diethyl 2-(5-bromo-3-nitropyridin-2-yl)malonate (31.8 g, 88 mmol) in aqueous hydrochloric acid (6M, 1.4 L) was stirred at reflux for 18 hours. The reaction mixture was cooled to ambient temperature and added very slowly to a saturated aqueous solution of aqueous sodium bicarbonate (4 L) at 0° C. The mixture was then extracted with dichloromethane (7 L), dried over magnesium sulfate and the solvent removed in vacuo to give 5-bromo-2-methyl-3-nitropyridine as an orange oil (13.8 g, 63.9 mmol, 72percent) which solidified upon standing. 1HNMR (300 MHz, CDCl3): δ ppm 8.78 (s, 1H), 8.43 (s, 1H), 2.79 (s, 3H). |
72% | Stage #1: for 18 h; Reflux Stage #2: With sodium hydrogencarbonate In water at 0℃; |
A mixture of the diethyl 2-(5-bromo-3-nitropyridin-2-yl)malonate (31 .8 g, 88 mmol) in aqueous hydrochloric acid (6M, 1 .4 L) was stirred at reflux for 18 hours. The reaction mixture was cooled to ambient temperature and added very slowly to a saturated aqueous solution of aqueous sodium bicarbonate (4 L) at 0 °C. The mixture was then extracted with dichloromethane (7 L), dried over magnesium sulfate and the solvent removed in vacuo to give 5-bromo-2-methyl-3-nitropyridine as an orange oil (13.8 g, 63.9 mmol, 72 percent) which solidified upon standing. 1HNMR (300 MHz, CDCI3) : ppm 8.78 (s, 1 H), 8.43 (s, 1 H), 2.79 (s, 3H). |
72% | Stage #1: With hydrogenchloride In water for 18 h; Reflux Stage #2: With sodium hydrogencarbonate In water at 0℃; |
A mixture of the diethyl 2-(5-bromo-3-nitropyridin-2-yl)malonate (31.8 g, 88 mmol) in aqueous hydrochloric acid (6 M, 1.4 L) was stirred at reflux for 18 hours. The reaction mixture was cooled to ambient temperature and added very slowly to a saturated aqueous solution of aqueous sodium bicarbonate (4 L) at 0° C. The mixture was then extracted with dichloromethane (7 L), dried over magnesium sulfate and the solvent removed in vacuo to give 5-bromo-2-methyl-3-nitropyridine as an orange oil (13.8 g, 72percent) which solidified upon standing. 1HNMR (300 MHz, CDCl3, δ): 8.78 (s, 1H), 8.43 (s, 1H), 2.79 (s, 3H). |