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CAS No. : | 55-22-1 | MDL No. : | MFCD00006429 |
Formula : | C6H5NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | TWBYWOBDOCUKOW-UHFFFAOYSA-N |
M.W : | 123.11 | Pubchem ID : | 5922 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 31.2 |
TPSA : | 50.19 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) : | -6.82 cm/s |
Log Po/w (iLOGP) : | 0.76 |
Log Po/w (XLOGP3) : | 0.32 |
Log Po/w (WLOGP) : | 0.78 |
Log Po/w (MLOGP) : | -1.13 |
Log Po/w (SILICOS-IT) : | 0.75 |
Consensus Log Po/w : | 0.3 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.23 |
Solubility : | 7.21 mg/ml ; 0.0586 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.94 |
Solubility : | 14.2 mg/ml ; 0.116 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.35 |
Solubility : | 5.46 mg/ml ; 0.0444 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
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 |
---|---|---|
80% | Reflux | Isonicotinic acid (0.1 mol), sulfuric acid (0.12 mol) and anhydrous methanol (0.12 mol), was added to a 150 ml single-necked flask, the reaction was heated to reflux, after the end of the reaction, spin off the solvent, washed with water to prepare 12.08 g of isonicotinate as shown in formula (II), Yield 80percent. |
75% | for 6 h; Reflux | General procedure: A catalytic amount of concentrated H2SO4 wasadded to a solution of carboxylic acids 16(a–j) (1.0 mmol)in 50 mL of methanol, and the mixture was refluxed for 6 h. It was allowed to cool. The saturated solution ofNaHCO3 was added to the reaction mixture, and it wasextracted with EtOAc (2 X 50 mL). The combined organiclayer was dried Na2SO4 and concentrated to obtain puremethyl esters 17(a–j). |
2.82 g | at 0 - 5℃; for 3 h; Inert atmosphere; Reflux | Thionyl chloride (0.7 mL, 0.009 mole) was added drop wise to a stirred suspension of isonicotinic acid (5 g, 0.04 mole) in methanol (50 mL) under N2 at 0 - 5 °C. The reaction mixture was then refluxed for 3 hours to obtain a clear solution. The reaction mass was cooled to RT and concentrated to obtain a residue that was diluted with water (20 mL) and extracted with ethyl acetate (100 mL x 3). The organic extracts were combined, washed with aqueous sodium bicarbonate (10 mL), brine (20 mL) dried over anhydrous Na2SC>4 and concentrated under vacuum to obtain the crude compound that was further purified by flash chromatography using ethyl acetate: hexane (40:60) to obtain methyl isonicotinate. Yield: 2.82 g; lH - NMR (CDC13, 400 MHz) δ ppm: 3.96 (s, 3H); 7.83 - 7.85 (d, J = 5.3 Hz, 2H), 8.77 - 8.78 (d, J = 5.2 Hz, 2H); Mass (m/z): 138.0 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.4% | With hydrazine dihydrochloride In aq. phosphate buffer at 30℃; for 1 h; Enzymatic reaction | Fed-batch biotransformation was carried out in 250ml Erlenmeyer flask containing 50ml of reaction mixture with initial isonicotinamide and hydrazine–2HCl concentration of 100 and 1000mM respectively in phosphate buffer (100mM, pH 7) at 30°C and 2.0mgdcw/ml resting cells of B. smithii strain IITR6b2. Powdered isonicotinamide (0.61g) and highly concentrated solution (1ml, 5M, pH 7) of hydrazine–2HCl were fed in subsequent seven feeds at an interval of 60min to restrict the residual isonicotinamide and hydrazine–2HCl concentration above 100 and 1000mM respectively. 500μl of sample was withdrawn at every 30min during the reaction and monitored for isoniazid, isonicotinic acid and isonicotinamide concentration. Effort was made to maintain the reaction volume constant around 50ml. A control experiment was also conducted with same parameters without enzyme for any spontaneous chemical reaction |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | Stage #1: for 2 h; Reflux Stage #2: With potassium carbonate In tetrahydrofuran at 20℃; for 24 h; |
A solution of isonicotinic acid (14, 5.0 g, 40.6 mmol) in thionyl chloride (40 mL) was heated at reflux for 2 h. After completion of the reaction, thionyl chloride was removed under reduced pressure. THF (50 mL), K2CO3 (16.8 g, 121.9 mmol) and aniline (3.78 g, 40.6 mmol) were added to the residue and the reaction mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with water (100 mL) and extracted with EtOAc (2 x 100 mL). The combined organic layer was concentrated and the residue was recrystallized from EtOAc-hexanes (60:40) to afford the product 15 (8.0 g, 99percent) as a light yellow solid: mp 166-168 °C. IR (KBr) 1344, 1653, 1465, 665 cm 1; *H NMR (DMSO-ifc, 300 MHz) δ 10.49 (s, 1 H), 8.78 (m, 2 H), 7.86 (m, 2 H), 7.78 (m, 2 H), 7.39 (t, = 8.0 Hz, 2 H), 7.15 (t, = 6.5 Hz, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | Stage #1: With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 40℃; for 2.5 h; Stage #2: for 20 h; |
A solution of 1,10-carbonyldiimidazole (130 g,0.81 mol), isonicotinic acid (100 g, 0.81 mol) and DMF (300 mL) was heated at 40 C for 2.5 h before aniline (100 g, 0.81 mol) was added in a single portion. After 20 h, water (1.2 L) was added. The resulting suspension was filtered andthe solids dried under vacuum to afford isonicotinanilide (39) (142.6 g, 89percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | Stage #1: With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 2 h; Stage #2: With toluene-4-sulfonic acid In ethanolHeating / reflux |
25 g (203 mmol) Isonicotinsaeure, 35.12 g (243.7 mmol) 2, 2-Dimethyl-1, 3-dioxolan- 4,6-dion und 49.6 g (406 mmol) 4-Dimethylaminopyridin werden in 300 [ML] Dichlor- methan vorgelegt und auf [0°C] gekuehlt. Es wird eine 1N Loesung von 46.1 g (223.4 mmol) 1, 3-Dicyclohexylcarbodiimid in Dichlormethan zugetropft. Es wird 2 Stunden bei Raumtemperatur nachgeruehrt. Der entstandene Niederschlag wird abfiltriert und mit Dichlormethan nachgewaschen. Das Filtrat wird im Vakuum eingeengt. Der Rueckstand wird in 1200 ml Ethanol geloest und mit einer Loesung aus 96.6 g (507.7 mmol) p-Toluolsulfonsaeure-monohydrat in 300 ml Ethanol versetzt und eine Stunde unter Rueckfluss geruehrt. Nach dem Abkuehlen wird das Ethanol im Vakuum abgezogen. Der Rueckstand wird in 1000 ml Ethylacetat und 900 ml Wasser aufgenommen und in der Hitze geloest. Die organische Phase wird abgetrennt, mit 600 ml gesaettigter Natriumhydrogencarbonatloesung und gesaettigter Natriumchlorid- loesung gewaschen und ueber Natriumsulfat getrocknet. Es wird im Vakuum eingeengt. Das Rohprodukt wird ueber eine Kieselgel-Fritte mit Dichlormethan-Methanol 10 : 1 filtriert. Da die waessrige Phase noch Produkt enthaelt, wird diese mit Dichlormethan extrahiert, ueber Natriumsulfat getrocknet und im Vakuum eingeengt. Das Roh- produkt wird ueber eine Kieselgel-Fritte mit Dichlormethan-Methanol 10 : 1 filtriert. Insgesamt erhaelt man 25.9 g (42 percent d. Th. ) Produkt. [1H-NMR] (300 MHz, DMSO-d6) : [5] = 1.17 (t, 3H), 4.12 (q, 2H), 4.25 (s, 2H), 7.82 (dd, 2H), 8.83 (dd, 2H) LC-MS (Methode 3) : [RT =] 2.40 min MS (ESIpos) : [M/Z =] 194 [(M+H) +] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | Stage #1: With magnesium chloride In tetrahydrofuran at 50℃; Stage #2: With 1,1'-carbonyldiimidazole In tetrahydrofuran for 18 h; |
To ethyl potassium malonate (6.25 g, 36.7 mmol) in THF (30 mL) was added MgCl2 (2.71 g, 28.4 mmol) and the mixture heated to 50° C. In another flask, CDI (6 g, 36.6 mmol) was added to a solution of isonicotinic acid (3 g, 24.4 mmol) in THF (30 mL) at 10° C. This mixture was stirred at 25° C. for 1 h, after which it was added to the ethyl potassium malonate/MgCl2 suspension and stirred for 18 h. Upon completion, water was added, and the aqueous mixture extracted with EtOAc (3*50 mL). The organic phase was washed with brine, dried over Na2SO4, concentrated, and the crude material purified by column chromatography (30percent EtOAc-Hexane) to give 3-Oxo-3-pyridin-4-yl-propionic acid ethyl ester (1.2 g, 25percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With magnesium chloride In tetrahydrofuran | 1.1. Preparation of Ethyl 3-(4-pyridyl)-3-oxopropionate Isonicotinic acid (35.56 g, 289 mmol) was added to a solution of 1,1'-carbonylbis-1H-imidazole (46.98 g, 290 mmol) in tetrahydrofuran (700 ml), and the resulting solution was stirred for 1.5 hr at 50° C. After cooling to room temperature, malonic acid monoester potassium salt (51.7 g, 304 mmol) and magnesium chloride (34.33 g, 361 mmol) were added, and the mixture was refluxed for 1 hr and then heated at 50° C. for 6 hr. The solvent was removed under reduced pressure and the residue was quenched by the addition of dilute acetic acid. The organic layer was extracted with ethyl acetate (3 times) and the combined extracts were washed with dilute aqueous sodium bicarbonate and brine, and were concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=2/1 to 1/1) and recrystallization from hexane-ethyl acetate gave 41.52 g (74percent) of the title compound. |
74% | With magnesium chloride In tetrahydrofuran | 1.1. Preparation of Ethyl 3-(4-pyridyl)-3-oxopropionate Isonicotinic acid (35.56 g, 289 mmol) was added to a solution of 1,1'-carbonylbis-1H-imidazole (46.98 g, 290 mmol) in tetrahydrofuran (700ml), and the resulting solution was stirred for 1.5 hr at 50°C. After cooling to room temperature, malonic acid monoester potassium salt (51.7 g, 304 mmol) and magnesium chloride (34.33 g, 361 mmol) were added, and the mixture was refluxed for 1 hr and then heated at 50°C for 6 hr. The solvent was removed under reduced pressure and the residue was quenched by the addition of dilute acetic acid. The organic layer was extracted with ethyl acetate (3 times) and the combined extracts were washed with dilute aqueous sodium bicarbonate and brine, and were concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate = 2/1 to 1/1) and recrystallization from hexane - ethyl acetate gave 41.52 g (74percent) of the title compound. |
74% | With magnesium chloride In tetrahydrofuran | 1.1. Preparation of Ethyl 3-(4-pyridyl)-3-oxopropionate Isonicotinic acid (35.56 g, 289 mmol) was added to a solution of 1,1'-carbonylbis-1H-imidazole (46.98 g, 290 mmol) in tetrahydrofuran (700ml), and the resulting solution was stirred for 1.5 hr at 50°C. After cooling to room temperature, malonic acid monoester potassium salt (51.7 g, 304 mmol) and magnesium chloride (34.33 g, 361 mmol) were added, and the mixture was refluxed for 1 hr and then heated at 50°C for 6 hr. The solvent was removed under reduced pressure and theresidue was quenched by the addition of dilute acetic acid. The organic layer was extracted with ethyl acetate (3 times) and the combined extracts were washed with dilute aqueous sodium bicarbonate and brine, and were concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate = 2/1 to 1/1) and recrystallization from hexane - ethyl acetate gave 41.52 g (74percent) of the title compound. |
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