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CAS No. : | 38533-61-8 | MDL No. : | MFCD00130268 |
Formula : | C6H5ClN2O3 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | DVRGUTNVDGIKTP-UHFFFAOYSA-N |
M.W : | 188.57 | Pubchem ID : | 2795029 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-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 |
---|---|---|
61% | With trimethylamine; In methanol; at 120℃; for 24h; | 2-Chloro-6-methoxy-3-nitropyridine (0.13 g, 0.69 mmol)5-Amino-1H-benzotriazole (0.09 g, 0.69 mmol) and triethylamine (0.11 mL, 0.76 mmol) were dissolved in methanol and the mixture was stirred at 120 ° C for 24 hours. After cooling in the atmosphere, water was added slowly and stirred for 30 minutes. The resulting solid product was filtered off, washed with methanol and dried to give compound 5e (61percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; for 2h;Inert atmosphere; | A mixture of 2-chloro-6-methoxy-3-nitropyridine (1.89 g, 10 mmol), <strong>[109-11-5]morpholin-3-one</strong> (1.01 g, 10 mmol), Xantphos (578 mg, 1.0 mmol), Pd2(dba)3 (457 mg, 0.5 mmol), Cs2CO3 (6.5 g, 20 mmol), in 1,4-dioxane (50 mL) was stirred under nitrogen at 100 C for 2h. The mixture was then cooled to room temperature and filtered through Celite. The filtrate was concentrated and purified by flash chromatography (3:1 petroleum ether:ethyl acetate) to afford 4-(6- methoxy-3-nitropyridin-2-yl)<strong>[109-11-5]morpholin-3-one</strong> (1.2 g, yield 47%) as a yellow solid. LCMS (ESI) [M+H] = 254.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.21% | With hydrogenchloride; tetrabutyl-ammonium chloride; In N,N-dimethyl acetamide; water; at 80℃; for 1h; | To a stirred solution of 6-methoxy-2-chloro-3-nitro pyridine(1 ; 5.0 g, 26.596 mmol) in dimethyl acetamide (75ml_) was added sodium 4-chlorobenzene-sulphinate (2;7.92g, 39.894 mmol) and tetra-N-butylammonium chloride (2.22g, 7.979 mmol) and Cone HCI 0.75 ml at room temperature. The reaction mixture was stirred at 80C for 1 hour. Progress of reaction was monitored by LCMS. The whole reaction mixture was poured on crushed ice to get solid. This solid compound was filtered through sintered funnel and thoroughly dried under vacuum to isolate 2-((4-Chlorophenyl)sulfonyl)-6-methoxy- 3-nitropyridine as desired product (7.1 g, 81.21 %). 1H NMR (400 MHz, CDCI3) d 8.10 (d, J= 8.6 Hz, 1 H), 8.0 (d, J= 7.9 Hz, 2H), 7.56 (d, J= 7.9 Hz, 2H), 6.95 (d, J= 8.7 Hz, (1079) 1 H), 3.69 (s, 3H). LCMS [m/z (M+H)+ =(Calculated for C12H9N205SCI+H: 329) found: 329], Purity at l=220hht 98.73% |
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