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CAS No. : | 2169-99-5 | MDL No. : | MFCD01043210 |
Formula : | C8H9NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GJDGYWVSQUBDDP-WEVVVXLNSA-N |
M.W : | 167.16 | Pubchem ID : | 135460299 |
Synonyms : |
|
Signal Word: | Danger | Class: | 4.1,6.1 |
Precautionary Statements: | P240-P210-P241-P280-P370+P378-P501-P261-P270-P271-P264-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405 | UN#: | 2926 |
Hazard Statements: | H228-H301+H311+H331-H315-H319 | Packing Group: | Ⅱ |
GHS Pictogram: |
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* 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 |
---|---|---|
97% | With iron(III) chloride; silica gel; In neat (no solvent); at 110℃; for 2.0h;Green chemistry; | General procedure: Aldoxime (1.0 mmol) and anhydrous FeCl3 (1.0 mmol) were intimately mixed with silica gel 60-120 mesh (1.0 g) in mortar and pestle. The resulting solid mixture was poured into a round-bottom flask (50 ml) and allowed to stir on magnetic stirrer at 110 C for an appropriate time (Table 2). The progress of the reaction was monitored by thin-layer chromatography (TLC). After completion of the reaction, the reaction mixture was extracted with ethyl acetate (3 15 ml) and washed several times with water. The combined organic mixture was dried over anhydrous Na2SO4, concentrated, and purified by column chromatography on silica gel 60-120 mesh using petroleum ether/ethyl acetate as eluent to afford pure nitrile. |
4.55 g | In dimethyl sulfoxide; at 100℃; for 6.0h; | General procedure: Salicylaldehyde 1A (28.86g, 1 equiv.) was dissolved in DMSO (200ml) to give an orange solution. Hydroxylamine hydrochloride (29.31g, 2.2 equiv.) was charged and stirred at RT for 20 min to give a yellow solution, this was heated to 100 C for 6 hrs before being allowed to cool. Reaction was quenched into water (300ml) and extracted with diethyl ether (5x 100ml). Combined organic was washed with brine (2x 50ml), dried (Mg2SO4) and stripped to give a foul smelling red-brown solid (30.53g). Semi-pure material suitable for subsequent reactions was obtained by extraction of impurities into refluxing heptane (100ml) followed by cooling and tituation. Pure material for characterisation was obtained by flash chromatography (product adhered to silica, eluting with 1:9 EtOAc in hexane, Rf = 0.32) which yielded the title compound as a orange-red solid (20.58g, 73%) |
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