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CAS No. : | 6628-86-0 | MDL No. : | MFCD00007289 |
Formula : | C7H4ClNO3 | Boiling Point : | - |
Linear Structure Formula : | C6H3(Cl)(NO2)CHO | InChI Key : | SWGPIDCNYAYXMJ-UHFFFAOYSA-N |
M.W : | 185.57 | Pubchem ID : | 81123 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-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 |
---|---|---|
70% | With vasicine; In ethylene glycol; at 80℃; for 48.0h; | General procedure: The mixture of nitrocompound (0.5 mmol) and vasicine (0.5 mmol) in ethylene glycol (2 mL) was stirred at 80C for 24-48 h. Time was not optimized separately for all substrates. After completion of reaction as monitored by TLC, the reaction mixture was cooled to ambient temperature and extracted with ethyl acetate. The ethyl acetate layer was dried under reduced pressure using rotatory evaporator. The crude was chromatographed over silica gel to afford the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Preparation of 1-tert-butyl 3-methyl 4-(5-chloro-2-nitrobenzyl)piperazine-1,3-dicarboxylate (52)1.5 g (8.2 mmol) of the aldehyde 51 and 2.0 g (8.2 mmol) of the amine 5 are initially introduced in a mixture of 50 ml of dichloroethane and 50 ml of THF. 0.940 ml of glacial acetic acid are then added, and the mixture is stirred at RT for about 3 h. 5.5 g (24.6 mmol) of NaB(OAc)3 and a further 0.940 ml of acetic acid are subsequently added, and the mixture is stirred overnight at room temperature. The batch is stirred with saturated NaHCO3 solution, diluted with dichloromethane and extracted by shaking. The organic phase is again washed by shaking with water, the aqueous phase is again extracted by shaking with DCM. The combined organic phases are dried over Na2SO4, filtered off with suction and evaporated to dryness in vacuo. The 3.5 g of crude product obtained are dissolved in THF, adsorbed onto Isolute and separated on silica gel 60 (Flashmaster). The relevant fractions are combined and evaporated to dryness in a rotary evaporator, thus giving the desired product 52 (1.6 g, 21% yield) in a purity of 45% (mass: [M+]=414; HPLC method D, RT=3.86 min) as yellow oil, which is reacted further without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With triphenylphosphine; In diphenylether; at 260℃; for 1h; | General procedure: In a 50 ml round bottom flask containing magnetic stir bar was charged with o-nitro benzaldehydes (2 mmol), phosphorane (2.2 mmol), triphenyl phosphine (4.6 mmol) and diphenyl ether (10 mL) and heated at 260 oC for 1 h. The reaction mass was then cooled to room temperature and poured on silica column. Products were isolated by eluting with petrolium ether to 3:1 pet ether: ethyl acetate. |
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