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CAS No. : | 77820-58-7 | MDL No. : | MFCD06797833 |
Formula : | C8H8ClNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MSXSZFYRADEEJA-UHFFFAOYSA-N |
M.W : | 185.61 | Pubchem ID : | 11030511 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 47.14 |
TPSA : | 52.32 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) : | -5.65 cm/s |
Log Po/w (iLOGP) : | 1.97 |
Log Po/w (XLOGP3) : | 2.51 |
Log Po/w (WLOGP) : | 1.72 |
Log Po/w (MLOGP) : | 1.91 |
Log Po/w (SILICOS-IT) : | 1.61 |
Consensus Log Po/w : | 1.94 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.81 |
Solubility : | 0.287 mg/ml ; 0.00155 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.25 |
Solubility : | 0.103 mg/ml ; 0.000556 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.73 |
Solubility : | 0.344 mg/ml ; 0.00185 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.41 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
75% | Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2.16667 h; Stage #2: With water; sodium sulfate In tetrahydrofuran at 0℃; |
(2-Amino-3-chlorophenyl)methanol. A solution of methyl 2-amino-3-chlorobenzoate (1.7 g, 9.16 mmol) in THF (40 mL) was dropwise added to a suspension of the LAH (521 mg, 13.7 mmol) in THF (15 mL) at room temperature over 10 min under N2, and stirred for 2 hrs. The reaction was carefully quenched with saturated Na2SO4 (10 mL) at 0° C., extracted with Et2O (2.x.50 mL). The combined organic layers were washes with brine (30 mL), dried on MgSO4, and concentrated on rotary vacuum to afford the expected product as a yellow solid (1.08 g, 75percent), which was pure enough to be used in the next step without further purification; 1H NMR (400 MHz, CDCl3) δ ppm 1.65 (s, 1H), 4.59-4.70 (m, 4H), 6.60-6.65 (m, 1H), 6.96 (dd, J=7.55, 1.26 Hz, 1H), 7.19-7.25 (m, 1H); Mass spec. 158.02 (MH+), Calc. for C7H8ClNO2 157.03. |
75% | Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2.16667 h; Stage #2: With water In tetrahydrofuran |
(2-Amino-3-chlorophenyl)methanol; A solution of methyl 2-amino-3-chlorobenzoate(1.7 g, 9.16 mmol) in THF (40 mL) was dropwise added to a suspension of the LAH(521 mg, 13.7 mmol) in THF(15 mL) at room temperature over 10 min under N2, and stirred for 2 hrs. The reaction was carefully quenched with saturated Na2SO4 (10 mL) at 0° C., extracted with Et2O (2.x.50 mL). The combined organic layers were washes with brine(30 mL), dried on MgSO4, and concentrated on rotary vacuum to afford the expected product as a yellow solid(1.08 g, 75percent), which was pure enough to be used in the next step without further purification; 1H NMR (400 MHz, CDCl3) δ ppm 1.65 (s, 1 H), 4.59-4.70 (m, 4 H), 6.60-6.65 (m, 1 H), 6.96 (dd, J=7.55, 1.26 Hz, 1 H), 7.19-7.25 (m, 1 H); Mass spec. 158.02 (MH+), Calc. for C7H8ClNO2 157.03. |
67% | With sodium hydroxide In hexane; water | EXAMPLE 81 Preparation of 2-amino-3-chlorobenzyl alcohol A solution of 28.9 g (155 mmol) of methyl 3-chloro-anthranilate in 100 ml of ether was added dropwise to a stirred suspension of 7.67 g (202 mmol) of lithium aluminum hydride in 400 ml of ether. After stirring for 5 hours at room temperature, the grey mixture was treated sequentially with 7.7 ml of water, 7.7 ml of 15percent sodium hydroxide and 23 ml of water. The reaction mixture was filtered, and the filtrate was evaporated at reduced pressure. The oily residue was dissolved in ether, and precipitation of the product was induced by addition of hexane. The product was collected by filtration to yield a tan solid in 67percent yield, m.p. 56°-68° C. IR and 1 H NMR spectra were in agreement with the assigned structure. Analysis: Calculated for C7 H8 ClNO: C, 53.35; H, 5.12; N, 8.88; Found: C, 53.16; H, 4.84; N, 9.28. |
67% | With sodium hydroxide In hexane; water | EXAMPLE 97 Preparation of 2-amino-3-chlorobenzyl alcohol A solution of 28.9 g (155 mmol) of methyl 3-chloroanthranilate in 100 ml of ether was added dropwise to a stirred suspension of 7.67 g (202 mmol) of lithium aluminum hydride in 400 ml of ether. After stirring for five hours at room temperature, the grey mixture was treated sequentially with 7.7 ml of water, 7.7 ml of 15percent sodium hydroxide and 23 ml of water. The reaction mixture was filtered, and the filtrate was evaporated at reduced pressure. The oily residue was dissolved in ether, and precipitation of the product was induced by addition of hexane. The product was collected by filtration to yield a tan solid in 67percent yield, mp 56°-68° C. IR and 1 H NMR spectra were in agreement with the assigned structure. Analysis: Calculated for C7 H8 ClNO: C, 53.35; H, 5.12; N, 8.88. Found: C, 53.16; H, 4.84; N, 9.28. |
67% | With sodium hydroxide In hexane; water | Example 81 - Preparation of 2-amino-3-chlorobenzyl alcohol A solution of 28.9 g (155 mmol) of methyl 3-chloro-anthranilate in 100 ml of ether was added dropwise to a stirred suspension of 7.67 g (202 mmol) of lithium aluminum hydride in 400 ml of ether. After stirring for 5 hours at room temperature, the grey mixture was treated sequentially with 7.7 ml of water, 7.7 ml of 15percent sodium hydroxide and 23 ml of water. The reaction mixture was filtered, and the filtrate was evaporated at reduced pressure. The oily residue was dissolved in ether, and precipitation of the product was induced by addition of hexane. The product was collected by filtration to yield a tan solid in 67percent yield, mp 56-68°C. IR and 1H NMR spectra were in agreement with the assigned structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With iron; acetic acid In ethanol at 20℃; for 2 h; Heating / reflux | Methyl 2-amino-3-chlorobenzoate. Iron powder (1.94 g, 34.8 mmol) was added to the solution of methyl 3-chloro-2-nitrobenzoate (2.5 g, 111.6 mmol) in EtOH/HOAc (100 mL/100 mL) at room temperature, and then the suspension was refluxed under N2 for 2 hrs. After cooling down to room temperature, partial of the solvents was removed on rotary vacuum, the resulting residue was partitioned between H2O/EtOAc (200 mL/300 mL). The separated organic phase was washed with aqueous NaOH (1N, 50 mL), brine (50 mL), dried over MgSO4, and concentrated on rotary vacuum to afford the expected product as a tan oil (1.7 g, 79percent yield) which became wax type solid standing on bench. The crude product was pure enough to be used in next step without further purification; 1H NMR (400 MHz, CDCl3) δ ppm 3.86 (s, 3H), 6.25 (s, 2H), 6.57 (t, J=7.93 Hz, 1H), 7.39 (dd, J=7.81, 1.51 Hz, 1H), 7.79 (dd, J=8.06, 1.51 Hz, 1H); Mass spec. 185.95 (MH+), Calc. for C8H8ClNO2 185.02. |
79% | Stage #1: With iron; acetic acid In ethanol at 20℃; for 2 h; Heating / reflux Stage #2: With sodium hydroxide In water; ethyl acetate |
Methyl 2-amino-3-chlorobenzoate; Iron powder (1.94 g, 34.8 mmol) was added to the solution of methyl 3-chloro-2-nitrobenzoate (2.5 g, 11.6 mmol) in EtOH/HOAc (100 mL/100 mL) at room temperature, and then the suspension was refluxed under N2 for 2 hrs. After cooling down to room temperature, partial of the solvents was removed on rotary vacuum, the resulting residue was partitioned between H2O/EtOAc (200 mL/300 mL). The separated organic phase was washed with aqueous NaOH (1N, 50 mL), brine (50 mL), dried over MgSO4, and concentrated on rotary vacuum to afford the expected product as a tan oil (1.7 g, 79percent yield) which became wax type solid standing on bench. The crude product was pure enough to be used in next step without further purification; 1H NMR (400 MHz, CDCl3) δ ppm 3.86 (s, 3 H), 6.25 (s, 2 H), 6.57 (t, J=7.93 Hz, 1 H), 7.39 (dd, J=7.81, 1.51 Hz, 1 H), 7.79 (dd, J=8.06, 1.51 Hz, 1 H); Mass spec. 185.95 (MH+), Calc. for C8H8ClNO2 185.02. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With tetrabutylammomium bromide; potassium carbonate In toluene at 80℃; for 1 h; | 5.13 g (0.03 mol) of 2-amino-3-chlorobenzoic acid, ml of toluene, 0.97 g (0.003 mol) of tetrabutylammonium bromide, and 4.54 g (0.04 mol) of dimethyl sulfate were added to a 100 ml four-necked flask equipped with a stirrer, a reflux condenser, a thermometer, and a dropping funnel, and a mixture of 4.56 g (0.033 mol) of potassium carbonate and 9 ml of toluene was added dropwise with stirring at 80° C. Then, the mixture was stirred at 80° C. for 1 hour. The solution was analyzed by HPLC by the absolute calibration method, and as a result, the yield was 96percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.5% | With potassium carbonate In methanol | EXAMPLE 5 Preparation of methyl 3-chloroanthranilate 98.8 g (0.5 mol) of 3-chloroisatoic anhydride and 9.0 g of potassium carbonate are stirred, at 25° C., into 250 g of methanol, and the mixture is stirred at this temperature for a further 3 h. Subsequently, it is filtered, washed with methanol and the methanol is distilled off under atmospheric pressure, and 87.7 q of methyl 3-chloroanthranilate are distilled at 115° C./15 mbar. This corresponds to a yield of 94.5percent of theory. The purity by GC is >99.5percent. s.p.: 37.5° C. MS: 185 (M30), 153 (M30 --CH3 OH), 125 |
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