Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 86692499 | HCID 86692499 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86692501 | HCID 86692501 | 39.3% |
Reaction Steps
To a solution of 1-(6-cyclopropylpyridin-3-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (910 mg) in methanol (3 ml) and tetrahydrofuran (5 ml) were added 4 N aqueous solution of sodium hydroxide (7 ml) and water (3 ml), and stirred at room temperature overnight. After completion of the reaction, the organic solvent was evaporated in vacuo, then water and diethyl ether were added thereto, and the aqueous layer was separated. To the aqueous layer was added concentrated hydrochloric acid under ice-cooling to adjust the layer to pH 5, and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated in vacuo. To the obtained residue were added ethyl acetate and n-hexane, the precipitated solid was collected by filtration, washed with ethyl acetate/n-hexane solution, and heat-dried in vacuo at 60° C. to give the titled compound (321 mg) as a pale yellow solid. MS (ESI) m/z: 244 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09150555B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-32ef4397810e42c9a0e7eb7ea890a91e |
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| Source note | uspto-grants-2015_10 |
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