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CAS No. : | 103796-34-5 | MDL No. : | MFCD11044852 |
Formula : | C11H13NO6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 255.22 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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 |
---|---|---|
85% | With nitric acid; tin(ll) chloride In dichloromethane at -25℃; for 0.0833333h; | 4 To a mixture of 11.4 ml of Tin(IV) chloride (0.097 mol) and 0.1 ml of fumming nitric acid (0.155 mol) in 100 ml of dichloromethane was added dropwise 17 g of compound 15 (0.08 mol) in 100 ml of dichloromethane at -25° C. with stirring. After 5 min, 200 ml of water was added and the product was extracted with dichloromethane and ethyl acetate. The organic layer was dried over MgSO4 and concentrated to give compound 16 (16.4 g, 85%). 1H-NMR (300 MHz, CDCl3): δ 7.28 (s, 1H), 6.82 (s, 1H), 4.13 (m, 4H), 1.46 (m, 6H). |
67% | With nitric acid; acetic acid at 20℃; for 2.08333h; | |
27% | With nitric acid; acetic acid at 20℃; for 1h; |
27% | With nitric acid; acetic acid at 20℃; for 1h; | A 4,5-diethoxy-2-nitrobenzoic acid General procedure: A flask immersed in a room-temperature water bath was charged with 3,4- diethoxybenzoic acid (1 .29 g. 6.1 mmol) and acetic acid (glacial, 5.2ml_). HNO3 (70%, 5.4 mL) was slowly added and stirred for 60 min at room temperature. The reaction was quenched upon addition of ice. A yellow precipitate formed that was filtered and washed with H2O. Recrystallization from DCM gave 4,5-diethoxy-2- nitrobenzoic acid as an off-white solid (424 mg, 1 .7 mmol, 27%). 1 H NMR (600 MHz, CDCIs) δ 10.29 (s, 1 H), 7.37 (s, 1 H), 7.24 (s, 1 H), 4.24 - 4.17 (m, 4H), 1 .51 (t, J = 7.0 Hz, 6H). 13C NMR (151 MHz, CDCI3) δ 170.6, 151 .6, 150.9, 142.2, 1 19.0, 1 12.5, 108.1 , 65.4, 65.4, 14.5, 14.4. HRMS (+) calcd for (M+H)+ 256.0816. Found 256.0818. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 44 percent / SnCl2; aq. HCl / 2 h / 20 °C 2: 57 percent / 80 - 200 °C 3: 73 percent / oxalyl chloride; DMF / 1,2-dichloro-ethane / 2.5 h / Heating |