Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 1H-Pyrazol-3-amine, 5-methyl- | HCID 93146 | — |
| Reactant | HCID 86680294 | HCID 86680294 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Product | HCID 178469359 | HCID 178469359 | 35% |
Reaction Steps
A mixture of 3-amino-5-methylpyrazole (50.0 g), diethyl oxalate sodium salt (127.3 g) and acetic acid (113 mL) in 1N hydrochloric acid (625 mL) was stirred at 80° C. for 14 h, then refluxed for 3 h, cooled to r.t., and the precipitate formed was filtered by suction filtration and dried in vacuum at 60° C. The crude product was stirred in 500 mL ethyl acetate at r.t. and the solid was filtered off and dried in air. 6-Hydroxy-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester (40.2 g, 35%) was obtained as pale yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09133181B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-df0184b23cfd4df38f80868d949d46d2 |
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| Source note | uspto-grants-2015_09 |
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