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CAS No. : | 2011-09-8 | MDL No. : | MFCD17015364 |
Formula : | C7H3Cl2NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 236.01 | 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 |
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With chromium(VI) oxide; sulfuric acid at -15℃; |
Yield | Reaction Conditions | Operation in experiment |
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at -15℃; |
Yield | Reaction Conditions | Operation in experiment |
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97% | Stage #1: 4,5-dichloro-2-nitrobenzoic acid With thionyl chloride for 0.166667h; Heating / reflux; Stage #2: With ammonia In tetrahydrofuran | 2.20 Example 2.20; 2-(1-Benzofuran-2-yl)-6,7-dichloro-4(3H)-quinazolinone (C: R=6,7-diCI, R'=1-benzofuran-2-yl); 4,5-Dichloro-2-nitrobenzoic acid (1.665 g, 7.05 mmol) was refiuxed in thionyl chloride (25 mL) for 10 min. The solvent was removed in vacuo and the residue was dissolved in thf (20 mL), ammonia gas was bubbled through the solution until conversion to the amide was complete. The solvent was removed in vacuo and the residue was partitioned between EtOAc/water, removal of the solvent from the organic layer gave 4,5-dichloro-2-nitrobenzamide (1.60 g, 97%). 1H NMR (DMSO-d6) 8 ppm 8.37 (s, 1H), 8.21 (bs, 1H), 7.97 (s, 1H), 7.84 (bs, 1H). ACPI-MS Found: [M+H]+= 236. |
Yield | Reaction Conditions | Operation in experiment |
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77% | With lithium hydroxide; water In tetrahydrofuran; methanol for 1h; | 36.C C. 4,5-Dichloro-2-nitrobenzoic acid piperidine amide A solution of 4,5-dichloro-2-nitrobenzoic acid methyl ester (0.29 g, 1.16 mmol) in 1:1 THF/methanol (4 mL) was stirred as 1 N aqueous LiOH (2 mL) was added. [0245] After 1 h, the mixture was acidified with 1 N HCl and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated to provide crude 4,5-dichloro-2-nitrobenzoic acid as a light yellow solid (0.26 g, 0.90 mmol, 77%). The acid was refluxed in 4 mL thionyl chloride for 2 h, and the crude reaction mixture was concentrated in vacuo. Residual thionyl chloride was removed by the repeated addition and in vacuo stripping of DCM. The acid chloride was placed under high vacuum for 10 min, and then taken up in dry DCM (5 mL). The mixture was cooled in an ice bath. Piperidine (0.46 g, 5.4 mmol, 0.53 mL) was added, and the reaction mixture was allowed to stand at 0° C. overnight. The mixture was diluted with DCM, washed with 1 N HCl (2×), 5% aqueous NaHCO3 and brine, and dried (MgSO4). Filtration and concentration provided 0.32 g of the desired amide, which could not be separated from an impurity (10%) that corresponded to the product of displacement of a chlorine by an additional equivalent of piperidine. HPLC (reversed-phase): RT=9.35 min (90%), 10.58 (10%). MS (ESI): major m/z 303 [M+H]+, minor m/z 352 [M+H]+. |
With lithium hydroxide In tetrahydrofuran; methanol for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride for 2h; | ||
With thionyl chloride for 2h; Heating / reflux; | 36.C C. 4,5-Dichloro-2-nitrobenzoic acid piperidine amide A solution of 4,5-dichloro-2-nitrobenzoic acid methyl ester (0.29 g, 1.16 mmol) in 1:1 THF/methanol (4 mL) was stirred as 1 N aqueous LiOH (2 mL) was added. [0245] After 1 h, the mixture was acidified with 1 N HCl and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated to provide crude 4,5-dichloro-2-nitrobenzoic acid as a light yellow solid (0.26 g, 0.90 mmol, 77%). The acid was refluxed in 4 mL thionyl chloride for 2 h, and the crude reaction mixture was concentrated in vacuo. Residual thionyl chloride was removed by the repeated addition and in vacuo stripping of DCM. The acid chloride was placed under high vacuum for 10 min, and then taken up in dry DCM (5 mL). The mixture was cooled in an ice bath. Piperidine (0.46 g, 5.4 mmol, 0.53 mL) was added, and the reaction mixture was allowed to stand at 0° C. overnight. The mixture was diluted with DCM, washed with 1 N HCl (2×), 5% aqueous NaHCO3 and brine, and dried (MgSO4). Filtration and concentration provided 0.32 g of the desired amide, which could not be separated from an impurity (10%) that corresponded to the product of displacement of a chlorine by an additional equivalent of piperidine. HPLC (reversed-phase): RT=9.35 min (90%), 10.58 (10%). MS (ESI): major m/z 303 [M+H]+, minor m/z 352 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18 4,5-Dichloro-2-nitrobenzoic acid (25) and 2,5-Dichloro-4-nitrobenzoic acid (26) EXAMPLE 18 4,5-Dichloro-2-nitrobenzoic acid (25) and 2,5-Dichloro-4-nitrobenzoic acid (26) A mixture of 308 g (0.881 mol) of the malonates from Example 15, 150 ml of HOAc, 50 ml of water, and 150 ml of conc. HCl was heated at reflux for 2 days and then cooled to room temperature. The precipitate was collected by filtration, washed with water, treated with 200 ml of conc. HNO3 and the mixture refluxed for 2 days. The solution was cooled to room temperature and the light yellow precipitate was filtered, washed with water, and dried in vaccum. The benzoic acids obtained consisted of compounds 25 and 26 in a ratio of 1.8:1 (total yield: 170 g, 82%). Compound 25: 1 H-NMR from DMSO-d6 (δ ppm): 8.02 (S, 1H), 8.17 (S, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In diethylene glycol dimethyl ether; mineral oil | 1 4-Chloro-5-(4-chlorophenoxy)-2-nitrobenzoic Acid PREPARATION 1 4-Chloro-5-(4-chlorophenoxy)-2-nitrobenzoic Acid To 30 ml of dry diglyme under a nitrogen atmosphere was added 0.960 g (0.02 mol) of sodium hydride dispersion in mineral oil (50%). The solution was cooled to 10° C. and 1.28 g (0.01M) 4-chlorophenol in 15 ml of dry diglyme was added dropwise while maintaining the temperature at 10° C. This was followed by the dropwise addition of 2.36 g (0.01 mol) of 4,5-dichloro-2-nitrobenzoic acid in 15 ml of dry diglyme. The reaction mixture was then heated to 153° C. (oil bath) for 1 hour and 45 minutes. The reaction mixture was cooled to room temperature and poured into an ice/water mixture. The pH was then adjusted to 1.5 with 6N hydrochloric acid. The solution was extracted with ethyl acetate, and the organic layer dried over anhydrous magnesium sulfate. The solvent was removed and the crude solid triturated with hexane, followed by recrystallization from carbon tetrachloride to give the title compound: yield 1.65 g (50%) m.p. 160°-162° C. By the same method, the following other 2-nitrobenzoic acids were prepared from the appropriate Y1 substituted phenol and 5-X1 substituted 2-nitrobenzoic acid: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: thionyl chloride / 0.17 h / Heating / reflux 2: iron; acetic acid / ethanol; water / 0.17 h / Heating / reflux |