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CAS No. : | 7477-10-3 | MDL No. : | MFCD09027297 |
Formula : | C6H3ClN2O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HCRHNMXCDNACMH-UHFFFAOYSA-N |
M.W : | 202.55 | Pubchem ID : | 346459 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
In dichloromethane; at 0℃; | To a suspension of 49.0 g (0.27 mol) 6-hydroxy-5-nitro-nicouenic acid in thionyl chloride (240 mi) are added 2 ml of DMF. This mixture is stirred at 60°C until the evolution of gaz has ended. Then it is stirred at 80°C for further 18 h. Residual thionyl chloride is removed under vacuo and the resulting residue is coevaporated three times with toluene. Subsequently this reaction mixture is dissolved in dichloromethane (100 mi) and cooled to 0°C before methanol (55.5 ml) is dropwise added. The precipitated solid is filtered off and dried under vacuo at 50°C to give 27.6 g (13.7 mmol/52 percent) of the title compound as a light yellow solid with a melting point of 78°C (dichloromethane/methanol). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(Trimethylsi.yl)diazomethane (8.25 mL of a 2.00 M solution in hexanes, 16.5 mmol) was added in three portions to a stirred solution of delta-chloro-S-nitronicotinic acid (1.00 g, 4.95 mmol) in methanol (12.0 mL) and DCM (24.0 mL) at 0 °C. The reaction mixture was quenched with TFA and concentrated in vacuo to afford the title compound i-2a . mlz (ES) 217 (MH)+. 1H NMR (500 MHz, CDCl3): delta 9.20 (d, 1H, J= 2.1 Hz), 8.79 ((L IR J= 2.1 Hz), 4.05 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 24h; | Methyl 6-chloro-5-nitronicotinate was purchased from Sigma Aldrich or synthesized as follows. Toa solution of 6-chloro-5-nitronicotinic acid (Ark Pharm, Inc., 2.5 g, 12.3 mmol) in dry DMF (30mL) were added K2CO3 (2.5 g, 18.5 mmol) and iodomethane (8.76 g, 61.7 mmol). The solution wasstirred at room temperature for 24 h, then poured onto ice, and extracted with EtOAc (100 mL × 3).The organic layer was washed with H2O (100 mL × 2) and brine (100 mL), and dried over MgSO4.The solvent was evaporated under reduced pressure and the residue was purified by flash columnchromatography (EtOAc/n-hexane = 1/2) to afford 10 (2.4 g, 92percent) as a yellow solid. |
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