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CAS No. : | 619-84-1 | MDL No. : | MFCD00002537 |
Formula : | C9H11NO2 | Boiling Point : | - |
Linear Structure Formula : | HO2CC6H4N(CH3)2 | InChI Key : | YDIYEOMDOWUDTJ-UHFFFAOYSA-N |
M.W : | 165.19 | Pubchem ID : | 12092 |
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 |
---|---|---|
87% | With thionyl chloride; for 5h; | General procedure: To a solution of the benzoic acid derivative (10 mmol) in anhydrous methanol (35 mL)was added dropwise thionyl chloride (1.1 mL, 15 mmol) under vigorous stirring (stirbar). After 5 h, about 25 mL of the methanol was distilled off and the residue was pouredonto 50 mL of ice water. Then saturated aqueous sodium bicarbonate was added withstirring until the evolution of carbon dioxide ceased. The resulting precipitate wascollected and recrystallized from methanol. |
80% | With bromobenzene; at 55 - 60℃; under 3750.38 - 4500.45 Torr; for 8h;Autoclave; | General procedure: benzoic acid (Table 3, entry 1) (1.0 g,0.0081 mol), bromobenzene (0.125 g, 0.0081 mol), 10% palladium on carbon(50% wet) (0.2 g) and methanol (3 mL) were placed in autoclave vessel. Autoclave was pressurized with 1-2 bar of nitrogen followed by 1-2 bar of hydrogen gas and then put under the desired pressure of hydrogen (5-6 bar).The reaction mixtures are then warmed to 55-60 C temperature and stirredfor 4 h at 300 rpm. After reaction, the catalyst was filtered through celite bed.Filtrate was added with water (30 mL). The reaction mixture was extracted with isopropyl acetate (2 15 mL). The combined organic layers were washedwith 5% aqueous sodium bicarbonate solution (2 15 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was evaporated under vacuum togive of methyl benzoate product Methyl 4-(dimethyl amino)benzoate: Colorlesssolid: 100-102 oC; 1H NMR (400 MHz, CDCl3):d = 7.96-7.85 (m, 2 H), 6.70-6.59 (m, 2 H), 3.86(s, 3 H), 3.04 (s, 6 H). 13CNMR (100 MHz, CDCl3): delta 40.0, 51.4, 110.7, 117.0, 131.2, 153.2, 167.5 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; water; | PREPARATION 19 Methyl p-Dimethylaminobenzoate p-Dimethylaminobenzoic acid (50 g.) and concentrated H2 SO4 (25 ml.) in 350 ml. methanol were refluxed 18 hours. The reaction mixture was cooled, quenched with ice and water (350 ml.), neutralized portionwise with KHCO3 until foaming ceased, and extracted 3*200 ml. CHCl3. The organic layers were combined, washed 1*150 ml. brine, dried (MgSO4) and reduced in volume to yield crystalline title product, 52 g.; 1 H-nmr: 3.02 (s, 6H), 3.87 (s, 3H), 6.66 (d, J=16Hz, 2H), 7.95 (d, J=16Hz, 2H). |
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