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CAS No. : | 524-38-9 | MDL No. : | MFCD00005891 |
Formula : | C8H5NO3 | Boiling Point : | - |
Linear Structure Formula : | HON(CO)2C6H4 | InChI Key : | CFMZSMGAMPBRBE-UHFFFAOYSA-N |
M.W : | 163.13 | Pubchem ID : | 10665 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-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 |
---|---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 3h;Inert atmosphere; | General procedure: To a solution of alcohol (1mmol) in freshly distilled THF (5ml) was added triphenylphosphine (1.1mmol) and N-hydroxylphthalimide (1.1mmol). After the solution was cooled to 0°C diisopropylazodicarboxylate (1.1mmol) was added dropwise. The solution was allowed to warm to room temperature over 3h. Reaction progress was monitored by TLC (1:1 heptanes:ethyl acetate). Hydrazine monohydrate (1.1mmol) was then added and the solution was allowed to stir for 30min. The resulting reaction mixture was filtered to remove the white precipitate. The filtrate was concentrated and subjected to flash chromatography (1:1 heptanes/ethyl acetate). The resulting product was dissolved in ether and treated with HCl (2.0M solution in ether) to afford the HCl salt of the O-alkylhydroxylamine. Contaminating diisopropyl hydrazinodicarboxylate could be washed away from the HCl salt with dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26.2% | With N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 12h; | Cooling to 0 ° C, 2-hydroxyisoindole-1,3-dione 2a (2.5 g, 15.33 mmol), 3-(pyrrolidin-1-yl)propanol 2b (1.98 g, 15.33 mmol, well known Method of "Catalysis Communications, 2007, 8 (11), 16711674 "Prepared" and triphenylphosphine (4.02 g, 15.33 mmol) were dissolved in 50 mL of tetrahydrofuran, and N,N-diisopropylethylamine (3.1 g, 15.33 mmol) was added dropwise, and the mixture was stirred at room temperature for 12 hours. The reaction solution was concentrated under reduced pressure. The obtained residue was concentrated under reduced pressure, and then filtered, and then filtered.The resulting residue was purified by eluent system A using a CombiFlash rapid preparation apparatus.The title compound 2c (1.1 g) was obtained.Yield: 26.2percent. |