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CAS No. : | 145959-21-3 | MDL No. : | MFCD02684307 |
Formula : | C9H10ClNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PIEZXKIADRCNNE-UHFFFAOYSA-N |
M.W : | 199.63 | Pubchem ID : | 22321939 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | 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 |
---|---|---|
90% | With tert.-butylhydroperoxide; copper(II) acetate monohydrate; calcium carbonate In acetonitrile at 80℃; for 24 h; | General procedure: An oven-dried 15 mL glass vial with a magnetic stirrer bar was charged with Cu(OAc)2·H2O (12 mg, 6 molpercent), N,O-dimethylhydroxylamine hydrochloride (2; 117 mg, 1.2 mmol), the respective benzyl alcohol 1 (1 mmol), aq 70percent TBHP (0.17 mL, 1.2 mmol), CaCO3 (120 mg, 1.2 mmol) in MeCN (1 mL). The glass vial was flushed with N2 three times and the contents were stirred at r.t. for 1 h. Then the reaction mixture was stirred for 24 h at 80 °C. After completion of the reaction, the mixture was cooled to r.t. All volatiles were removed under vacuum. The product was extracted with EtOAc (20 mL) and the organic layer was washed with sat. aq NaHCO3 (20 mL), dried (Na2SO4), and the solvent removed under vacuum. The Weinreb amide product 3 was purified by column chromatography (silica gel, 100–200 mesh) using a gradient of petroleum ether (bp 60–80 °C) and EtOAc. All the amides were identified by GC-MS, 1H, and 13C NMR spectroscopic analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 3 h; | General procedure: To a solution of 3-cyanobenzoic acid 8a (3.0 g, 19.7 mmol) in DMF was added N,O-dimethylhydroxylamine hydrochloride (2.0 g, 20.7 mmol), Et3N (2.88 mL, d = 0.73, 20.7 mmol) and EDC*HCl (4.0 g, 20.7 mmol). After the mixture was stirred for 3 h at room temperature, the solvent was removed in vacuo and the residue was dissolved in EtOAc, washed with 10percent citric acid, 10percent NaHCO3 and saturated NaCl, and dried over Na2SO4. Then, the solvent was removed to give a colorless oil of compound 9a (3.0 g, 79percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10.6 g | With triethylamine In dichloromethane at 20℃; for 2.66667 h; Inert atmosphere; Cooling with ice | 10306] To a cooled (ice bath) solution of N-methyl-O-methylhydroxylamine hydrochloride (6.13 1 g, 62.85 mmol) and triethylamine (20 mE, 142.85 mmol) in dry DCM (under Ar atmosphere) was added 3-chlorobenzoyl chloride (7.32 mE, 57.14 mmol) via slow dropwise addition. The mixture was stirred for 10 mins and then warmed to ambient temperature. Afier 2.5 h of stirring, the solvent was partially removed (condense about 80percent-rotary evaporator). The remainder was taken up in EA, washed successively with iN HC1 (twice) and 2M aqueous sodium carbonate, and then diluted a brine solution. The aqueous phases were back-extracted. The organic phases were combined, dried with magnesium sulfate, filtered and concentrated to give E-1 (10.6 g), which was used directly in the next step without thrther purification. |
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