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CAS No. : | 130250-62-3 | MDL No. : | MFCD02684312 |
Formula : | C10H13NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 195.22 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 | UN#: | N/A |
Hazard Statements: | H315-H319 | 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 |
---|---|---|
88% | With pyridine; carbon tetrabromide; triphenylphosphine In dichloromethane for 0.166667h; Ambient temperature; | |
86% | Stage #1: 2-Methoxybenzoic acid With NBS; triphenylphosphine In dichloromethane at 0℃; for 0.25h; Stage #2: O,N-dimethyl-hydroxylamine hydrochloride With triethylamine In dichloromethane at 20℃; for 1h; chemoselective reaction; | General procedure for the synthesis of Weinreb amides General procedure: A. To a mixture of benzoic acid (50 mg, 0.41 mmol, 1 equiv), PPh3 (160 mg, 0.61 mmol, 1.5 equiv) and NBS (108.5 mg, 0.61 mmol, 1.5 equiv), CH2Cl2 (2 ml) was added and the reaction was stirred at 0 °C for 15 min. The reaction was brought to room temperature and N,O-dimethylhydroxylamine hydrochloride (59.5 mg, 0.61 mmol, 1.5 equiv) and Et3N (45.5 mg, 63 µl, 0.45 mmol, 1.1 equiv) were added and reaction was stirred for 1 h at room temperature. The reaction mixture was quenched with aqueous sodium bicarbonate solution and diluted with CH2Cl2. The bicarbonate washings were again extracted with CH2Cl2 and the combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure. Column chromatography was performed using EtOAc/Petroleum ether (1:5). |
84% | Stage #1: 2-Methoxybenzoic acid With chloroformic acid ethyl ester; triethylamine In dichloromethane at 10℃; for 0.833333h; Stage #2: O,N-dimethyl-hydroxylamine hydrochloride With triethylamine In dichloromethane at 10℃; for 1h; | 5.2.6 4-Fluoro-N-methoxy-N-methylbenzamide (3a) General procedure: Method C: a solution of ethyl chloroformate (3.40mL, 35.68mmol) in anhydrous dichloromethane (6mL) was added dropwise at 10°C to a solution of 4-fluorobenzoic acid (5.00g, 35.68mmol) and triethylamine (5mL, 35.68mmol) in anhydrous dichloromethane (50mL). This reaction mixture was stirred at 10°C for 50min, and then N,O-dimethylhydroxylamine hydrochloride (3.48g, 35.68mmol) and triethylamine (5mL, 35.68mmol) were added. The resulting mixture was stirred for 1h at 10°C and the suspension was taken up in water (150mL) and extracted with CH2Cl2 (150mL). The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was finally chromatographed on silica gel eluting with ethyl acetate:petroleum ether (gradient from 0/100 to 20/80 v/v) to give 77% of 3a as clear oil. |
79% | With N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 3h; | 4.2.4. N,2-Dimethoxy-N-methylbenzamide (9a) 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 10% citric acid, 10% NaHCO3 and saturated NaCl, and dried over Na2SO4. Then, the solvent was removed to give a colorless oil of compound 9a (3.0 g, 79%); 1H NMR (300 MHz, DMSO-d6) δ 7.42-7.36 (m, 1H), 7.21 (dd, J = 7.4, 1.7 Hz, 1H), 7.07 (d, J = 8.3 Hz, 1H), 6.98 (dd, J = 7.4, 7.4 Hz, 1H), 3.78 (s, 3H), 3.45 (br s, 1H), 3.07 (s, 3H), 3.19 (br s, 2H); HRMS (ESI): m/z 218.0795 [M+Na]+ (Calcd for C10H13NO3Na: 218.0793). |
Stage #1: 2-Methoxybenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 3h; Inert atmosphere; Stage #2: O,N-dimethyl-hydroxylamine hydrochloride With triethylamine In dichloromethane at 0℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With potassium phosphate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 100℃; for 20h; | |
89% | With potassium phosphate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 100℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | Stage #1: t-butyl phenyl ether; 2-methoxy-N-methoxy-N-methylbenzamide With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane at -78 - 20℃; Stage #2: 2-methoxy-N-methoxy-N-methylbenzamide In diethyl ether; hexane at 20℃; for 2h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With dmap; triethylamine; In acetonitrile; at 20℃; | 2-Methoxybenzoic acid (1a, 761 mg, 5.0 mmol), triethylamine (725 μL, 5.2 mmol), and 4-DMAP (61 mg, 0.5 mmol) was added to a solution of N-methoxy-N-methyl carbamoyl chloride (619 mg, 5.0 mmol) in acetonitrile at room temperature and stirred for 1.5 h. After evaporation of acetonitrile, the mixture was poured into saturated NaHCO3 solution (40 mL) and extracted with methylene chloride (3 × 25 mL). The condensed residue was purified with short pathway silica gel column chromatography using 50% EtOAc/n-hexane to give 2a (820 mg, 84%). 1H NMR (300 MHz, CDCl3) δ 7.33-7.39 (m, 1H),7.24-7.28 (m, 1H), 6.99 (d, J = 7.4 Hz, 1H), 6.91 (d,J = 6.4 Hz, 1H), 3.85 (s, 3H), 3.49 (s, 3H), 3.32 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 177.2, 155.8, 130.6, 127.7,125.3, 120.5, 111.2, 61.0, 55.7 (overlapped); FT-IR (film)1640 (C O) cm-1; MS m/z (%) 195 (M+, 2), 135 (100). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran at 0 - 20℃; Inert atmosphere; |