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CAS No. : | 603-11-2 | MDL No. : | MFCD00007138 |
Formula : | C8H5NO6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KFIRODWJCYBBHY-UHFFFAOYSA-N |
M.W : | 211.13 | Pubchem ID : | 69043 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 49.18 |
TPSA : | 120.42 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) : | -7.06 cm/s |
Log Po/w (iLOGP) : | -0.09 |
Log Po/w (XLOGP3) : | 0.75 |
Log Po/w (WLOGP) : | 0.99 |
Log Po/w (MLOGP) : | 0.23 |
Log Po/w (SILICOS-IT) : | -1.47 |
Consensus Log Po/w : | 0.08 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.72 |
Solubility : | 4.03 mg/ml ; 0.0191 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.86 |
Solubility : | 0.293 mg/ml ; 0.00139 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -0.53 |
Solubility : | 61.9 mg/ml ; 0.293 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.06 |
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 |
---|---|---|
83% | at 80 - 115℃; Autoclave | 2-nitrophthalic acid (100. 0 g), acetic anhydride (1 L) was added to a hydrogenation kettle, heated to 80 ° C,After the raw material disappeared, the mixture was cooled to room temperature, 10percent Pd / C (3 g) was added, replaced with nitrogen twice, hydrogen was introduced to IMPa,The reaction is maintained at room temperature until no hydrogen is absorbed, vented, blown with nitrogen,Heated to 110-115 ° C reaction to the raw material or intermediate state disappeared,Hot filter, cooled to 0-5 ° C, filtered, washed with glacial acetic acid to give pale yellow crystals, dried 80. 6g, yield 83percent, HPLC 99. 0percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.8% | for 1 h; Heating / reflux | A solution of 474.8 g (2.25 mol) of 3-nitrophthalic acid in 450 ml of acetic anhy- dride was stirred under reflux for 1 h. The solution was slowly cooled to 800C. Then 1000 ml of methyl-tert-butyl ether (MTBE) were added expeditiously and the solution EPO <DP n="34"/>was cooled to 15°C. The resulting solid was isolated, washed with MTBE and dried in a vacuum oven at 400C. Yield: 88.8percent |
88% | With oxalyl dichloride; N,N-dimethyl-formamide In toluene for 3 h; Inert atmosphere; Reflux | General procedure: Dicarboxylic acid 2 (1 mmol) and oxalyl chloride (1.2 mmol) were combined in dry toluene (5 mL) and a drop of freshly distilled DMF was added. The reaction vessel was purged with argon and the reaction was heated under stirring for 3 h. The stirring was stopped and the toluene solution was decanted off the oily residue and filtered. Evaporation of the volatiles provided the analytically pure target product which, if necessary, was transformed intro crystalline form by trituration with diethyl ether. In some cases (see ESI) additional crystallization or trituration with 1:2 v/v hexane-toluene mixture was used. . |
82% | With acetic anhydride In tert-butyl methyl ether for 1 h; Reflux | (1) Synthesis of 3-nitrophthalic anhydride (compound 2) 3-nitrophthalic acid (48.5 g, 0.23 mol) was mixed with acetic anhydride (45 mL), and the resulting mixture was stirred at reflux for 1 hour. After completion of the reaction, the mixture was cooled to 80° C., 100 mL of methyl tert-butyl ether was added to the mixture, and the mixture was continued to stir until cooled to 15° C. The mixture was filtered, and the resulted solid was washed with methyl tert-butyl ether and dried at 40° C. to give compound 2 as a white product (36.7 g, 82percent). |
74.0 g | With acetic anhydride In toluene at 25℃; Reflux | In to a well cleaned and 1.0L 4neck RB flask, 100.0g of 3-nitrophthalic acid and 60.36g of acetic anhydride, 500.0m1 of toluene were charged. Reaction mass was stirred for 5-10mm at 25-35°C.Reaction mass temperature was raised to reflux and maintained for 20-30min.after completion of reaction, reaction mass was cooled to 25-35°C, Reaction mass was stirred for 60-90 mm at 25-35°C. Solid reaction mass was filtered under vacuum, washing was given with40.0m1 of toluene, suck dried for 10-15mm. Wet compound was unloaded. Wet compound is dried in a vacuum oven, at 60-65°C, for 3.0-4.0 hours, under vacuum (600-65OmmJHg). Dried sample is transferred into a clean and dry polythene bag under nitrogen.Yield: 74.0g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86.2% | With sodium acetate; acetic acid In water at 116 - 118℃; for 16 h; | 40 ml of water, 70 g (331.6 mmol) of 3-nitrophthalic acid, 3-aminopiperidine-2,6-dione hydrochloride 53.5 g (325.0 mmol) Sodium acetate 27 g (329.3 mmol) and acetic acid (1200 ml) The reaction was stirred at 116-118 ° C for 16 h, Cooled to room temperature, Filter, filter cake water washing, Solid at 50-55 decompression (vacuum ≥ 0.08MPa) dry 4h, That is the target product 85g, For silver-gray solid, The yield was 86.2percent and the purity was 99.91percent. |
28.2 g | With 1,1'-carbonyldiimidazole In acetonitrile at 20 - 80℃; Inert atmosphere | Example 1: Synthesis of l,3-dioxo-2-(2,6-dioxopiperidin-3-yl)-4-nitro-isoindoline- dione (3-nitrophthalidomide) To the stirred mixture of 3-nitrophthalic acid (25.0 g or 0.12 mole) in acetonitrile (175 ml) was added 1 , 1 -carbonyldiimi dazole (CD1) (42,3 g or 0.26 mole) under nitrogen atmosphere at ambient temperature. To this mixture, 3-aminopiperidine 2,6-dione hydrochloride (19.5g or 0.12 mole) was added, and the reaction mixture was heated to 75 to 80 °C until the reaction was completed as monitored by TLC. After completion of the reaction, the solvent was distilled out under reduced pressure. Water (375 ml) was added to the reaction mass, and the reaction mass was slowly cooled at 0 to 5 °C while stirring. The isolated solid was filtered, washed with water, then by methanol, and suck dried. Finally the isolated solid was dried at 55 to 60 °C under vacuum until constant weight to obtain 3-nitrophthalidomide. Yield: 28.2 g, 78.5percent (molar) (HPLC purity -99.5percent) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | at 5℃; for 20 - 25 h; Heating / reflux | 3-Nitrophthalic acid (500 g, 2.37 moles) was added to 2500 ml of methanoland 260 ml of thionyl chloride below ambient temperature. The mixture washeated at reflux for about 24 hours and then was concentrated under reducedpressure, followed by expelling the excess thionyl chloride under nitrogen. 1500ml of toluene was mixed with the residue, and then filtered. The obtained solidwas dried at 60-70°C to get 522.0 grams (98percent) of methyl 2-carboxyl-3-nitrobenzoate, which was substantially free from 3-nitrodimethylphthalate; 500 g of 3-Nitrophthalic acid, and methanol (2.5 I) were charged in a roundbottom flask followed by cooling to about 5-10°C. 259.5 ml of thionyl chloride wasadded under stirring for about 60-90 minutes followed by heating to about 60-65°C and was maintained for about 20-25 hours. Solvent was distilled completelyat about 60-65°C; 1500 ml of toluene was added and stirred for about 5-6 hoursunder nitrogen atmosphere. Separated solid was filtered and washed with 500mlof toluene, followed by drying the solid at about 55-65°C for about 5-10 hours toafford 525 grams of 3-nitrophthalic acid-1-methylester compound of Formula (II). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.7% | With sulfuric acid In methanol at 59 - 65℃; for 15 - 20 h; Heating / reflux; Industry scale | 3-Nitrophthalic acid [NPA] (660 kg), trimethyl orthoformate (400 kg), concentrated sulfuric acid (115 kg) and methanol (1180 kg) were mixed, and the mixture was stirred with heating (59 to 65 °C) for about 15 to 20 hours under reflux.. The reaction solution was cooled, and concentrated at 40 °C or lower under reduced pressure.. The residue was cooled to 30 °C or lower, water (900 L) was added, and the mixture was cooled to 5 °C or lower.. The precipitated crystals were separated by a centrifuge, washed with water, and dried at 50 °C for about 50 hours to give methyl 2-carboxy-3-nitrobenzoate [MNA] (666.8 kg, 94.7 percent). mp. 166-168 °C 1H-NMR (200MHz, CDCl3) δ: 4.03 (3H, s), 7.74 (1H, t), 8.39 (1H, dd), 8.42(1H, dd) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With potassium carbonate In ethanol; sulfuric acid | REFERENCE EXAMPLE 66 Ethyl 2-carboxy-3-nitrobenzoate A solution of 3-nitrophthalic acid (35 g) in ethanol (300 ml) containing conc. sulfuric acid (20 ml) was heated for 24 hours under reflux. The solvent was distilled off, and the residue was poured into ice-water (700 ml), which was extracted with ethyl acetate. The organic layer was washed with water, which was extracted with an aqueous solution of potassium carbonate. The aqueous layer was made acidic with hydrochloric acid, followed by extraction with methylene chloride. The organic layer was washed with water and dried. The solvent was distilled off to give a solid product (29 g, 74percent), which was used in the subsequent reaction without purification. 1 H-NMR(90MHz,CDCl3) δ: 1.43(3H,t), 4.47(2H,q), 7.70(1H,t), 8.40(2H,d), 9.87(1H,br s). IR(Nujol)cm-1: 1725, 1535, 1350, 1300, 1270. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sodium hydroxide; acetic acid In water; acetone | 1) Reduction of 3-nitro-1,2-benzene dicarboxylic acid to 3-amino-1,2-benzene dicarboxylic acid. 21.1 g (0.1 moles) of 3-nitro-1,2-benzene dicarboxylic acid dissolved in 75 ml of water containing 8.2 g of NaOH, are placed in a 500 ml glass autoclave. The pH of the mixture is then adjusted to 8-9 by the addition of dilute acetic acid. One gram of PtO2 is then added pressurised under H2 at 4 atm, after flushing 4 times with nitrogen. The autoclave temperature is raised to 50° C. and the mixture is left to react for 24 hours. On completion the platinum oxide is then removed by filtration and 50 ml of conc. HCL are added to the filtrate. An addition of 200 ml of acetone is then made to the resultant opalescent solution to promote precipitation of the inorganic salts, which are then filtered off. The filtrate is finally concentrated until an opalescent solution is obtained, from which after cooling at 4° C., the reaction product is precipitated in the form of hydrochloride. After filtering and drying under vacuum, 19.5 g of 3-amino-1,2-benzene dicarboxylic acid hydrochloride are obtained, representing a 90percent yield. |
90% | With sodium hydroxide; acetic acid In water; acetone | 1) Reduction of 3-nitro-1,2-benzene dicarboxylic acid to 3-amino-1,2-benzene dicarboxylic acid. 21.1 g (0.1 moles) of 3-nitro-1,2-benzene dicarboxylic acid dissolved in 75 ml of water containing 8.2 g of NaOH, are placed in a 500 ml glass autoclave. The pH of the mixture is then adjusted to 8-9 by the addition of dilute acetic acid. One gramme of PtO2 is then added and the autoclave is pressurised under H2 at 4 atm, after flushing 4 times with nitrogen. The autoclave temperature is raised to 50°C and the mixture is left to react for 24 hours. On completion the platinum oxide is then removed by filtration and 50 ml of conc. HCL are added to the filtrate. An addition of 200 ml of acetone is then made to the resultant opalescent solution to promote precipitation of the inorganic salts, which are then filtered off. The filtrate is finally concentrated until an opalescent solution is obtained, from which after cooling at 4°C, the reaction product is precipitated in the form of hydrochloride. After filtering and drying under vacuum, 19.5 g of 3-amino-1,2-benzene dicarboxylic acid hydrochloride are obtained, representing a 90percent yield. The product structure is confirmed by IR and 1H-NMR spectroscope analysis. |
65 g | Stage #1: With 10% palladium on activated carbon; Degussa type; hydrogen In ethanol at 20 - 25℃; for 3 h; Autoclave Stage #2: With hydrogenchloride In acetone at 10℃; |
3-nitrophthalic acid (lOOgm) and 10percent Pd/C (3.2 gm) in ethanol (600ml) was charged in autoclave and hydrogen pressure of 4.0 kg applied for 3.0 hr at 20-25 °C in autoclave. The reaction mass was cooled to 20°C and filtered through hyflo bed. The filtrate was distilled under reduced pressure and to the residue acetone was charged. The reaction mass was cooled to 10°C and followed by addition of conc., hydrochloric acid and stirred. The solvent was removed under reduced pressure and acetonitrile was added. The reaction mass was cooled to 10°C and precipitated solid was filtered. The product was dried at 45-50°C under vacuum for 6 hr to obtain 65.0gm of 3-aminophthalic acid hydrochloride salt. |
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