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CAS No. : | 51135-73-0 | MDL No. : | MFCD01631119 |
Formula : | C7H9NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KOMSQTMQKWSQDW-UHFFFAOYSA-N |
M.W : | 155.15 | Pubchem ID : | 7009317 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.43 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 37.56 |
TPSA : | 52.33 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) : | -6.54 cm/s |
Log Po/w (iLOGP) : | 2.11 |
Log Po/w (XLOGP3) : | 0.99 |
Log Po/w (WLOGP) : | 1.16 |
Log Po/w (MLOGP) : | 0.33 |
Log Po/w (SILICOS-IT) : | 1.39 |
Consensus Log Po/w : | 1.2 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.56 |
Solubility : | 4.23 mg/ml ; 0.0273 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.68 |
Solubility : | 3.26 mg/ml ; 0.021 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.09 |
Solubility : | 1.26 mg/ml ; 0.00809 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.72 |
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 |
---|---|---|
99.9% | With sulfuric acid In o-tolyl acetic acid | EXAMPLE 4 Preparation of 5-Methylisoxazole-4-Carboxylic Acid A two-necked flask fitted with mechanical stirrer and a horizontal condenser for distillation was charged with 40.0 g of crude Ethyl-5-methylisoxazole-4-carboxylate and 44 g of 60percent sulfuric acid and the mixture was heated to 85° C. with continuous distillation of ethanol from the reaction product. After four hours of heating at 85° C., TLC showed the complete disappearance of the upper spot of ester. The mixture was allowed to cool in the refrigerator and the solid acid was filtered (16.5 g) Filtrate kept at room temperature for second crop. Acid was crystallized in 60 mL 2percent acetic acid-Toluene to obtain about 99.9percent pure acid (9.5 g). Mother liquor of the final crystallization was kept for second crop. Crystallization was accomplished by: The crude acid was taken in 2percent acetic acid-toluene mixture and heated for 30 minutes. Brown oil was separated at the bottom of the flask. The clear organic phase was neatly transferred and kept for crystallization. |
60% | With sulfuric acid In water at 20℃; for 20 h; Reflux | Ethyl-5-methylisoxazole-4-carboxylate 7 g (0.045 mol) was heated under reflux in aqueous sulphuric acid (20 percent v/v, 30 ml) for 16 hr followed by cooling to room temperature with stirring for 4 h. The crystallized solid product was filtered and washed using toluene followed by water and dried. The product then was crystallized from ethanol to produce 3.5 g (60 percent) of 5-Methylisoxazole-4-carboxylic acid as a white solid, mp. 147-148 °C (reported mp. 144-147 °C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With hydroxylamine In methanol; water at -5 - 30℃; for 2.5 h; Heating / reflux | Ethyl-5-methylisoxazole-4-carboxylate:Ethyl ethoxymethyleneacetoacetate, 110.00 g (0.59 mol) was taken in methanol (330 ml) and cooled to -5 0C and 50percent aqueous hydroxyl amine 39.03 g (0.59 mol on anhydrous basis) was added drop wise over a period of 1 hour at -5 to O0C. It was stirred for 30 minutes. The reaction mixture was allowed to attain temperature of 20 to 30 0C and then refluxed for 1 S hour. Solvent was removed under reduced pressure and the reaction mass was cooled to room temperature. n-Hexane (500 ml) was added and stirred for 30 minutes. Saturated sodium bicarbonate solution (100 ml) was added followed by water (400 ml) and stirred well. The organic layer was separated. The aqueous layer was re-extracted with n-hexane (2x200 ml). The combined organic layer was washed with water (2x250 ml). After removal of the solvent <n="8"/>72.5 g (79percent) of Ethyl-5-methylisoxazole-4-carboxylate was obtained as yellowish thick oil with 98.7 percent HPLC purity and having isomeric impurity less than 0.5 percent. |
78% | With hydroxylamine hydrochloride; sodium acetate In methanol; water at 0 - 20℃; | Solution of hydroxylamine hydrochloride (4.1 g, 0.059 mol) and sodium acetate (4.84 g, 0.059 mol) in water (10 ml) was added dropwise to a solution of compound 3 (11 g, 0.059 mol) in methanol (25 ml) at 0 °C. The mixture was stirred during overnight at room temperature followed by extraction with EtOAc (3 x 50 ml), the combined EtOAc extract was washed by aqueous sodium bicarbonate solution to minimize the impurities and dried over Na2SO4. After that the solvent was removed to afford 7.16 g (78 percent) of Ethyl-5-methylisoxazole-4-carboxylate as yellow oil, which was used directly in the next step. |