Structure of 521-73-3
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 521-73-3 |
Formula : | C9H5NO3 |
M.W : | 175.14 |
SMILES Code : | O=C1NC(C(C2=C1C=CC=C2)=O)=O |
MDL No. : | MFCD01717158 |
InChI Key : | YIOFGHHAURBGSJ-UHFFFAOYSA-N |
Pubchem ID : | 10640 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 |
* 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 |
---|---|---|
With sodium hydride; at 0℃; for 3.5h; | 3ml of concentrated sulfuric acid is placed in a 10ml beaker followed by adding 0.5ml of fuming nitric acid into slowly, the system is cooled in icewater bath. 500mg of compound III is added into the above solution when the temperature falls to less than 12C, it can be seen at once that the color of the reaction solution changes into deep red, the temperature also rises to more than 50C instantly. The raw material has disappeared by TLC analysis after 5 minutes, and the reaction is processed as follows: slowly adding 50ml of acetic ether to dilute the reaction solution, extracting with water, back-extracting the water phase with 30ml of acetic ether, washing the organic phases with water and saturated salt solution respectively, combining the organic phases, then drying, condensing, thereby obtaining product IV. 40mg of compound IV is dissolved in 1.5ml of anhydrous solvent (listed in the above), the system is cooled in icesalt bath. After the reaction is conducted for 30min upon adding 14mg of sodium hydride into the above solution, 0.20ml of benzyl chlorine is dropped into slowly. The reaction is processed as follows after progressed for 3 hours: extracting quickly with dichloromethane, drying, condensing, and the residue is applied on silica gel column (petroleum ether: acetic ether=8:1) to obtain compound V. |
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