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CAS No. : | 1417997-93-3 | MDL No. : | MFCD31619280 |
Formula : | C22H19NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ASHPRZYGCOMVHO-WYMLVPIESA-N |
M.W : | 345.39 | Pubchem ID : | 70676597 |
Synonyms : |
MDK-7933
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
Multi-step reaction with 3 steps 1: lithium hydroxide / methanol 2: triethylamine / tetrahydrofuran / 1 h / 20 °C 3: hydroxylamine hydrochloride; potassium hydroxide / methanol / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 1 h / 20 °C 2: hydroxylamine hydrochloride; potassium hydroxide / methanol / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
326 mg | With hydroxylamine hydrochloride; potassium hydroxide In methanol at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 6 h / Inert atmosphere 2: pyridine / dichloromethane / 2 h / 20 °C 3: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / N,N-dimethyl-formamide / 12 h / 90 °C 4: lithium hydroxide / methanol 5: triethylamine / tetrahydrofuran / 1 h / 20 °C 6: hydroxylamine hydrochloride; potassium hydroxide / methanol / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: pyridine / dichloromethane / 2 h / 20 °C 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / N,N-dimethyl-formamide / 12 h / 90 °C 3: lithium hydroxide / methanol 4: triethylamine / tetrahydrofuran / 1 h / 20 °C 5: hydroxylamine hydrochloride; potassium hydroxide / methanol / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / N,N-dimethyl-formamide / 12 h / 90 °C 2: lithium hydroxide / methanol 3: triethylamine / tetrahydrofuran / 1 h / 20 °C 4: hydroxylamine hydrochloride; potassium hydroxide / methanol / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | Stage #1: With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at 20℃; for 1h; Stage #2: With hydroxylamine hydrochloride; potassium hydroxide In tetrahydrofuran; methanol for 3h; | 2 (E)-N-Hydroxy-4-benzyloxy-2-methxycinnamide (8a). General procedure: KOH (1.23 g, 22.00 mmol) was added to a solution of NH2OH (1.53 g, 22.00 mmol) in MeOH (20 mL). The resulting solution was stirred in an ice bath for 1 h. Filtration to remove the white salt gave a solution of NH2OH in MeOH. A solution of 7a (3.12 g, 11.00 mmol) in freshly distilled THF (30 mL) was treated with ethyl chloroformate (1.58 mL, 16.50 mmol) and EtsN (3.06 mL, 22.00 mmol) and was stirred at room temperature for 1 h. The prepared free NH2OH solution was then added to the reaction, and stirring was continued for 3 h. The reaction was diluted with distilled water (100 mL), acidified with In HCl(aq) to pH 2- 3, and extracted with EtOAc (3 x 50 mL). The organic layer was dried (Na2S04) and filtered, and the solvent was removed in vacuo. The residue was purified by silica gel chromatography (EtOAc/n-hexane, 1:2-1 : 1) to give 8a (1.81 g, 55%) as a white solid: mp: 128-135 °C; XH NMR (500 MHz, [D6]DMSO): d=10.60 (s, 1 H), 8.89 (s, 1 H), 7.58 (d, J=15.9 Hz, 1 H), 7.45 (t, j=7.4 Hz, 2H), 7.42 (d, J= 8.5 Hz, IH), 7.38 (t, J=7.4 Hz, 2H), 7.33 (d, J=7.4 Hz, 1 H), 6.70 (d, j=1.9 Hz, IH), 6.64 (dd, J=1.9, 8.5 Hz, IH), 6.37 (d, J=15.9 Hz, 1 H), 5.14 (s, 2 H), 3.83 ppm (s, 3H); 13C NMR (125 MHZ, [D6]DMSO): d=161.6, 160.0, 137.2, 134.9, 129.6, 128.4, 127.9, 127.7, 116.9, 106.6, 99.2, 69.8, 55.2 ppm; HRMS-EI: m/z [M]+ calcd for Ci7H17N04: 299.1157, found: 299.1160. |