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CAS No. : | 2457-76-3 | MDL No. : | MFCD00007772 |
Formula : | C7H6ClNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MBDUKNCPOPMRJQ-UHFFFAOYSA-N |
M.W : | 171.58 | Pubchem ID : | 17154 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 42.82 |
TPSA : | 63.32 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.4 cm/s |
Log Po/w (iLOGP) : | 0.89 |
Log Po/w (XLOGP3) : | 1.33 |
Log Po/w (WLOGP) : | 1.63 |
Log Po/w (MLOGP) : | 0.48 |
Log Po/w (SILICOS-IT) : | 1.14 |
Consensus Log Po/w : | 1.09 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.08 |
Solubility : | 1.43 mg/ml ; 0.00833 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.26 |
Solubility : | 0.941 mg/ml ; 0.00548 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.02 |
Solubility : | 1.63 mg/ml ; 0.00948 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.18 |
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 |
---|---|---|
98% | at 0 - 20℃; for 32 h; | To a solution of 4-amino-2-chlorobenzoic acid (2 g, 1 1.66 mmol) in MeOH (55.5 mL) was added thionyl chloride (3.40 mL, 46.6 mmol) dropwise at 0°C. The resulting solution was stirred at rt. After 32h the solvent was removed. The crude product was taken up in EtOAc and washed with sat. aqueous NaHC03 and brine. The organic layer was dried over MgS04, filtered and evaporated to dryness to give intermediate 125a (2.146 g, 1 1.45 mmol, 98 percent yield) as white solid.1 H NMR (400 MHz, DMSO-c/6) δ ppm 7.64 (d, J=8.56 Hz, 1 H), 6.64 (d, J=2.20 Hz, 1 H), 6.51 (dd, J=8.80, 2.20 Hz, 1 H), 6.16 (bs, 2 H), 3.73 (s, 3 H). Intermediate 125b: methyl 2-chloro-4-cvanobenzoate |
97.4% | at 0℃; Heating / reflux | To a 200 mL MeOH solution of 4-amino-2-chlorobenzoic acid (12 g, 67.84 mmol) was added 2 equivalents of SOCl2 (11 mL, 135.7 mmol) at 0° C. The ice-water bath was removed after the addition and the reaction mixture was heated to reflux until the starting material had disappeared, as indicated by LC-MS. After the reaction was cooled back to RT, solvent and excess of SOCl2 were removed under reduced pressure. The residue was suspended in 10percent aqueous Na2CO3 solution. The precipitate that formed was filtered and washed with water until the washes became neutral. The filter cake was then re-dissolved in 200 mL of ethyl acetate, and the ethyl acetate layer was washed with water, brine, and dried over anhydrous Na2SO4. After concentrated under reduced pressure and vacuum drying, 12.27 g of product was obtained (97.4percent). M+H+(186). |
97% | for 18 h; Heating / reflux | Example E 4-Amino-2-chlorobenzoic acid methyl ester Acetyl chloride (2.5ml) was added drop-wise to a stirred solution of 4-amino-2-chlorobenzoic acid (2.22g, 12.9mmol) in methanol (75ml). The mixture was heated at reflux for 18h, cooled and reduced in vacuo. The residue was taken up in EtOAc, washed with saturated sodium hydrogen carbonate solution and brine, dried and reduced in vacuo to afford a beige solid identified as 4-amino-2-chlorobenzoic acid methyl ester, yield 2.32g, 97percent. |
20.9 g | Stage #1: at 0 - 20℃; for 0.5 h; Stage #2: for 18 h; Reflux |
To methanol at 0 °C was added dropwise acetyl chloride (314.7 mmol, 22.4 mL). After the addition of acetyl chloride, the reaction mixture was stirred at rt for30 mm, then 4-amino-2-chlorobenzoic acid 1(116.6 mmol, 20.0 g) was added in one portion. The reaction mixture was heated at reflux for 18 hours, cooled to 0 °C, and concentrated under vacuum. The residue was suspended in 250 mL of ethyl acetate, cooled to 0 °C, and saturated aqueous NaHCO3 was added (pH was 8). The mixture was partitioned and extracted with ethyl acetate (200 mL). Combined organic layers were washed with brine, dried over MgSO4, and concentrated under vacuum to afford 20.9 g of title compound as a yellow solid which was used as such in next step without purification. 1H NMR (400 MHz, CDCI3): 67.78 (d, J= 8.6 Hz, 1H), 6.70 (d, J= 2.3 Hz, 1H), 6.52 (dd, J= 8.6, 2.3 Hz, 1H), 4.09 (bs, 1H), 3.86 (s, 3H). LCMS (M+1) 186.1,188.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | Stage #1: With lithium hydroxide In tetrahydrofuran at 20℃; for 0.333333 h; Stage #2: for 2 h; Heating / reflux |
4-Amino-2-chloro-benzoic acid (2.50 g) and lithium hydroxide monohydrate (611 mg) were suspended in tetrahydrofuran (20 ml), and the suspension was stirred at room temperature for 20 min. Thereafter, dimethylsulfuric acid (1.38 ml) was added to the reaction mixture, and the mixture was stirred under reflux for 2 hr. The solvent was removed by distillation under the reduced pressure. Water was added to the residue, and the mixture was neutralized with a saturated aqueous sodium hydrogencarbonate solution and was extracted with diethyl ether. The diethyl ether layer was then washed with water and saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure to give methyl 4-amino-2-chloro-benzoate (1.68 g, yield 62percent). Methyl 4-amino-2-chloro-benzoate (1.68 g) and 5-methoxymethylene-2,2-dimethyl-[1,3]dioxan-4,6-dione (1.53 g) were dissolved in 2-propanol (25 ml), and the mixture was stirred at 100°C for 15.5 hr. The solvent was removed by distillation under the reduced pressure, and the residue was washed with diethyl ether to give methyl 2-chloro-4-[(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidenemeth yl)-amino]-benzoate (1.92 g, yield 63percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | for 18 h; Heating / reflux | Acetyl chloride (2.5 ml) was added drop-wise to a solution of 2-chloro-4-cyano-benzoic acid (2.22 g, 12.94 mmol) in methanol (75 ml) while stirring. The mixture was heated at reflux for 18 h, cooled and concentrated in vacuo. The residue was taken up in ethyl acetate, washed with saturated NaHCO3 and brine and concentrated in vacuo to give a beige solid identified as 4-amino-2-chloro-benzoic acid methyl ester (2.32 g, 97percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.5% | Stage #1: With dihydrogen peroxide In water at 40 - 50℃; for 3 h; Ionic liquid Stage #2: With potassium fluoride In water at 40 - 50℃; for 3 h; |
To a four-necked flask was charged with 4-amino-2-chlorobenzoic acid 0.56mol, ionic liquids and water 3mol 50mol, warmed to 40-50 ° C, was added 3mol hydrogen peroxide, the reaction 3h, continue to add potassium fluoride 5mol and Tungstophoric ammonium salt 0.08mol, stirred 3h, filtered, and the filtrate solvent was removed under reduced pressure and dried to give 2-chloro-4-fluoro-benzoic acid, yield 97.5percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With sodium nitrite In water; hydrogen bromide | Synthesis of 4-Bromo-2-chlorobenzoic Acid (3) Eighty-eight grams (F.W. 171.58, 513 mmol) of 4-amino-2-chlorobenzoic acid (2), 48percent hydrobromic acid (304 mL) and water (304 mL) were heated at 120° C. for one hour and dissolved to form a hydrobromate salt. Under stirring, the solution was cooled (ice-sodium chloride), and an aqueous solution (water, 250 mL) of 44.4 g (F.W. 69.00, 643 mmol) of sodium nitrite was added thereto while maintaining 5° C. or below. In a beaker 120.8 g (F.W. 80.79, 2.83 mmol) of copper bromide in 48percent hydrobromic acid (331 mL) was made 0° C. and the prepared diazonium salt solution was slowly added thereto with stirring so as not to foam. After completion of the addition, the resulting solution was heated in a hot water bath until the generation of nitrogen ceased. The reaction solution was cooled by standing and then, extracted with ethyl acetate. The extract was treated according to the conventional method to obtain 88.3 g (73percent) of a desired 4-bromo-2-chlorobenzoic acid (3). Melting Point: 152-160° C.; IR (KBr) νmax cm-1: 3090, 1682, 1578; 1H NMR (400 MHz, CDCl3) δ: 7.50 (1H, dd, J=8.5, 2.0 Hz, Ar-H), 7.69 (1H, J=2 Hz, Ar-H), 7.89 (1H, J=8.5 Hz, Ar-H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | at 20℃; for 2.5 h; | First, NaBH4 (1 mmol) was used as a reducing agent forthe conversion of Ag (+ 1) to Ag (0) in methanol at roomtemperature for 2 h. After that, the Ag/MMT was filtered andused as a catalyst. Then, in a typical procedure, a mixtureof 4-nitrophenol (0.1 mmol), KOH (0.15 mmol), isopropylalcohol (3 mL), and Ag/MMT catalyst (50 mg) 1.01 wtpercentwas stirred at room temperature for an appropriate time(Scheme 2). After the completion of the reaction (monitoredby GC), the catalyst was separated by filtration. The ensuingproduct was extracted with ethyl acetate and repeatedlywashed with water (3–4 times) to remove KOH. The resultingsolvent was evaporated to dryness in vacuum. |
24% | With iron; ammonium chloride In ethanol; water for 2 h; Reflux | Step 5a. 4-Amino-2-chlorobenzoic acid (compound 3002) A mixture of 2-chloro-4-nitrobenzoic acid (5.0 g, 24.8 mmol), iron powder (8.0 g, 142.9 mmol) and NH4Cl (7.6 g, 142.9 mmol) in EtOH/water (50/50 mL) was heated at reflux for 2 h. The hot mixture was filtered through Celite and washed with ethyl acetate. The mixture was separated and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate. The crude product was purified by column chromatography (hexanes/ethyl acetate: 5/1, 3/1, 1/1) to afford compound 3002 as a white solid (1.0 g, 24percent yield). 1H NMR (400 MHz, DMSO-d6): δ 6.04 (s, 2H), 6.49 (dd, J=8.4 Hz, 2.0 Hz, 1H), 6.61 (d, J=2.0 Hz, 1H), 6.63 (d, J=8.8 Hz, 1H), 12.21 (br, 1H). |
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