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CAS No. : | 50727-06-5 | MDL No. : | MFCD11101027 |
Formula : | C8H5NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NHXFINXXELODNV-UHFFFAOYSA-N |
M.W : | 163.13 | Pubchem ID : | 10558950 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 43.84 |
TPSA : | 66.4 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.73 cm/s |
Log Po/w (iLOGP) : | 0.65 |
Log Po/w (XLOGP3) : | 0.79 |
Log Po/w (WLOGP) : | -0.1 |
Log Po/w (MLOGP) : | 0.67 |
Log Po/w (SILICOS-IT) : | 1.03 |
Consensus Log Po/w : | 0.61 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.72 |
Solubility : | 3.11 mg/ml ; 0.0191 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.77 |
Solubility : | 2.8 mg/ml ; 0.0172 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.19 |
Solubility : | 1.05 mg/ml ; 0.00641 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.22 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P273-P301+P312+P330-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H412 | 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 |
---|---|---|
72% | With ammonium carbonate; hydrogenchloride; sodium hydroxide In conc. AcOH | Step 1. Synthesis of 5-hydroxyisoindoline-1,3-dione To a mixture of ammonium carbonate (5.28 g, 54.9 mmol) in conc. AcOH (25 mL) was slowly added 4-hydroxyphthalic acid (5.0 g, 27.45 mmol). The resulting mixture was heated at 120° C. for 45 min., then the clear, bright yellow mixture was heated at 160° C. for 2 h. The resulting mixture was maintained at 160° C. and was concentrated to approximately 15 mL, then was cooled to room temp. and adjusted pH 10 with a 1N NaOH solution. This mixture was cooled to 0° C. and slowly acidified to pH 5 using a 1N HCl solution. The resultant precipitate was collected by filtration and dried under reduced pressure to yield 5-hydroxyisoindoline-1,3-dione as a pale yellow powder as product (3.24 g, 72percent): 1H NMR (DMSO-d6) δ7.00-7.03 (m, 2H), 7.56 (d, J=9.3 Hz, 1H). |
72% | With ammonium carbonate; hydrogenchloride; sodium hydroxide In conc. AcOH | Step 1. Synthesis of 5-hydroxyisoindoline-1,3-dione To a mixture of ammonium carbonate (5.28 g, 54.9 mmol) in conc. AcOH (25 mL) was slowly added 4-hydroxyphthalic acid (5.0 g, 27.45 mmol). The resulting mixture was heated at 120° C. for 45 min., then the clear, bright yellow mixture was heated at 160° C. for 2 h. The resulting mixture was maintained at 160° C. and was concentrated to approximately 15 mL, then was cooled to room temp. and adjusted pH 10 with a 1N NaOH solution. This mixture was cooled to 0° C. and slowly acidified to pH 5 using a 1N HCl solution. The resultant precipitate was collected by filtration and dried under reduced pressure to yield 5-hydroxyisoindoline-1,3-dione as a pale yellow powder as product (3.24 g, 72percent): 1H NMR (DMSO-d6) δ 7.00-7.03 (m, 2H), 7.56 (d, J=9.3 Hz, 1H). |
72% | With ammonium carbonate; hydrogenchloride; sodium hydroxide In conc. AcOH | Step 1. Synthesis of 5-hydroxyisoindoline-1,3-dione To a mixture of ammonium carbonate (5.28 g, 54.9 mmol) in conc. AcOH (25 mL) was slowly added 4-hydroxyphthalic acid (5.0 g, 27.45 mmol). The resulting mixture was heated at 120° C. for 45 min., then the clear, bright yellow mixture was heated at 160° C. for 2 h. The resulting mixture was maintained at 160° C. and was concentrated to approximately 15 mL, then was cooled to room temp. and adjusted pH 10 with a 1N NaOH solution. This mixture was cooled to 0° C. and slowly acidified to pH 5 using a 1N HCl solution. The resultant precipitate was collected by filtration and dried under reduced pressure to yield 5-hydroxyisoindoline-1,3-dione as a pale yellow powder as product (3.24 g, 72percent): 1H NMR (DMSO-d6) δ 7.00-7.03 (m, 2H), 7.56 (d, J=9.3Hz, 1H). |
72% | With ammonium carbonate In hydrogenchloride; sodium hydroxide; conc. AcOH | Step 1. Synthesis of 5-hydroxyisoindoline-1,3-dione To a mixture of ammonium carbonate (5.28 g, 54.9 mmol) in conc. AcOH (25 mL) was slowly added 4-hydroxyphthalic acid (5.0 g, 27.45 mmol). The resulting mixture was heated at 120° C. for 45 min., then the clear, bright yellow mixture was heated at 160° C. for 2 h. The resulting mixture was maintained at 160° C. and was concentrated to approximately 15 mL, then was cooled to room temp. and adjusted pH 10 with a IN NaOH solution. This mixture was cooled to 0° C. and slowly acidified to pH 5 using a IN HCl solution. The resultant precipitate was collected by filtration and dried under reduced pressure to yield 5-hydroxyisoindoline-1,3-dione as a pale yellow powder as product (3.24 g, 72percent): 1H NMR (DMSO-d6) δ7.00-7.03 (m, 2H), 7.56 (d, J=9.3 Hz, 1H). |
72% | at 120 - 160℃; for 2.75 h; | Step 1. Synthesis of 5-hydroxyisoindoline-1,3-dione To a mixture of ammonium carbonate (5.28 g, 54.9 mmol) in conc. AcOH (25 mL) was slowly added 4-hydroxyphthalic acid (5.0 g, 27.45 mmol). The resulting mixture was heated at 120° C. for 45 min., then the clear, bright yellow mixture was heated at 160° C. for 2 h. The resulting mixture was maintained at 160° C. and was concentrated to approximately 15 mL, then was cooled to room temp. and adjusted pH 10 with a 1N NaOH solution. This mixture was cooled to 0° C. and slowly acidified to pH 5 using a 1N HCl solution. The resultant precipitate was collected by filtration and dried under reduced pressure to yield 5-hydroxyisoindoline-1,3-dione as a pale yellow powder as product (3.24 g, 72percent): 1H NMR (DMSO-d6) δ 7.00-7.03 (m, 2H), 7.56 (d, J=9.3 Hz, 1H). |
71% | at 120 - 160℃; for 2.75 h; | e) 5-Hydroxy-isoindole-1,3-dione; [0156] A mixture of 4-hydroxyphthalic acid (5.0 g, 27.0 mmol), acetic acid (25 mL), and ammonium carbonate (5.3 g, 55 mmol) was heated at 120[deg.] C. for 45 min followed by heating at 160[deg.] C. for 2 h. After cooling to room temperature, the reaction mixture was half-evaporated and then the reaction mixture was basified to pH 10 with 1 N NaOH followed by acidification to pH 5 at 0[deg.] C. with concentrated HCl. The resulting precipitate was filtered off, washed with water, dried at 60[deg.] C. under high vacuum over night, to afford the title compound (3.2 g, 71percent) as an off-white crystalline solid. MS: m/e=162.1 (M-H<+>). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With ammonium carbonate; hydrogenchloride; sodium hydroxide In conc. AcOH | Step 1. Synthesis of5-hydroxyisoindoline-1,3-dione To a mixture of ammonium carbonate (5.28 g, 54.9 mmol) in conc. AcOH (25 mL) was slowly added 4-hydroxyphthalic acid (5.0 g, 27.45 mmol). The resulting mixture was heated at 120° C. for 45 min., then the clear, bright yellow mixture was heated at 160° C. for 2 h. The resulting mixture was maintained at 160° C. and was concentrated to approximately 15 mL, then was cooled to room temp. and adjusted pH 10 with a 1N NaOH solution. This mixture was cooled to 0° C. and slowly acidified to pH 5 using a 1N HCl solution. The resultant precipitate was collected by filtration and dried under reduced pressure to yield 5-hydroxyisoindoline-1,3-dione as a pale yellow powder as product (3.24 g, 72percent): 1H NMR (DMSO-d6) δ 7.00-7.03 (m, 2H), 7.56 (d, J=9.3 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | Stage #1: With borane-THF In tetrahydrofuran at -5 - 80℃; for 19 h; Stage #2: With hydrogenchloride In methanol; water at 0 - 80℃; for 3 h; Stage #3: With triethylamine In methanol; water at 22℃; for 0.5 h; |
Preparation of 2,3-dihydro-5-hydroxy-1H-isoindole (7); tert-Butyl 5-hydroxy-1,3-dihydroisoindole-2-carboxylate (6): 750 ml of a 1M borane/THF solution are added dropwise to 20.4 g (125 mmol) of hydroxyisoindole-1,3-dione in 300 ml of THF (dry) at -5° C. over a period of 60 min. The mixture is subsequently stirred for 2 h at 22° C. and then for 16 h at 80° C. The mixture is then cooled to 0° C., before 100 ml of methanol (exothermic.) and 100 ml of 2M hydrochloric acid are slowly added. The resultant mixture is stirred for 3 h at 80° C., cooled to 22° C., and 100 ml of water are added. The aqueous solution is extracted three times with 150 ml of dichloromethane each time. 27.8 g (125 mmol) of di-tert-butyl dicarbonate and 12.6 g (125 mmol) of triethylamine are then added to this aqueous solution, and the mixture is then stirred for 30 min at 22° C. The mixture is subsequently extracted three times with 100 ml of dichloromethane each time, the organic phases are dried over sodium sulfate, filtered, and the filtrate is evaporated to dryness in vacuo. Trituration with petroleum ether gives 6.7 g (22percent) of pale-beige crystals; 1H-NMR (500 MHz, DMSO-d6/TFA-d1, 90° C.): δ [ppm] 7.093 (m, 1H), 6.709 (m, 2H), 4.486 (m, 4H), 1.457 (s, 9H); MW 235.3. |
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