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CAS No. : | 552330-87-7 | MDL No. : | MFCD09834642 |
Formula : | C8H5BrN2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 225.04 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H320-H335 | Packing Group: | N/A |
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 |
---|---|---|
82% | Stage #1: 1-(2-amino-5-bromophenyl)ethanone With hydrogenchloride In water at 0℃; for 0.25h; Stage #2: With sodium nitrite at 0℃; Reflux; | |
82% | Stage #1: 1-(2-amino-5-bromophenyl)ethanone With hydrogenchloride In water at 0℃; for 0.25h; Stage #2: With sodium nitrite In water at 0℃; Reflux; | 6-Bromocinnolin-4(1H)-one (15). In a 250 mL round bottom flask was added 1-(2-amino-5-bromophenyl)ethanone (8.34 g, 39.0 mmol), water (30 mL), and conc. hydrochloric acid (30 mL, 987 mmol). The mixture was cooled to 0° C. in an ice bath and allowed to stir for 15 minutes until a suspension resulted. Aqueous sodium nitrite (2M, 20 mL, 40.0 mmol) was then added dropwise with an addition funnel. The resulting solution was allowed to warm to room temperature over 1.5 hours and was stirred at room temperature overnight, then refluxed for 6 hours. The mixture was cooled to room temperature, water (200 mL) was added, and the mixture was extracted with ethyl acetate (3*200 mL). The combined organic layers were then washed with brine (50 mL), dried over sodium sulfate, filtered, and concentrated on to silica. The crude product was then purified by flash column chromatography using a gradient of 1-10% methanol in dichloromethane to yield 15 as a dark brown solid in 82% yield. 1H NMR (500 MHz, DMSO-d6) δ 14.09 (br. s., 1H), 8.09 (d, J=2.2 Hz, 1H), 7.92 (dd, J=8.8, 2.2 Hz, 1H), 7.79 (s, 1H), 7.71 (d, J=9.1 Hz, 1H). LCMS found 224.9 [M+H]+. |
With hydrogenchloride Diazotization.anschliessend Aufbewahren; |
With hydrogenchloride Diazotization.anschliessend Erwaermen; | ||
3.0 g | With hydrogenchloride; sodium nitrite In water for 6h; Heating; | |
Multi-step reaction with 2 steps 1.1: 0.5 h / 20 °C 2.1: hydrogenchloride / water; tetrahydrofuran / 1 h / 65 °C 2.2: 8 h / 0 °C / Reflux |