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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1894695Generated: November 4, 2026

Oxalic Acid → HCID 67355904, compound

https://huagongshe.com/reaction/1894695

Reaction equation

Participants

RoleNameHCIDCharge
ReactantOxalic AcidHCID 971—
ReactantSodium HydroxideHCID 14798—
ReactantSodium borohydrideHCID 4311764—
ReactantHCID 57867419HCID 57867419—
SolventEthanolHCID 702—
SolventWaterHCID 962—
SolventTetrahydrofuranHCID 8028—
Solventtert-Butyl methyl etherHCID 15413—
ProductHCID 67355904HCID 6735590469.3%

Reaction Steps

To a mixture of ethyl 5-{2-[(2,2-dimethylpropanoyl)amino]pyridin-3-yl}isoxazol-3-carboxylate (3.17 g, 10 mmol), ethanol (3 mL) and tetrahydrofuran (10 mL) was added sodium borohydride (0.38 g, 10 mmol) at room temperature, which was stirred overnight under a ice cooling to room temperature. The reaction mixture was divided equally into five, among which one was added to 5N aqueous sodium hydroxide (2 mL), which was stirred overnight at 55° C. To the reaction mixture was added water, which was extracted with a mixture of methyl-tert-butylether and tetrahydrofuran, and oxalic acid (0.18 g, 2 mmol) was added to the organic layer. The precipitated solid was filtered to obtain the title compound (0.39 g) as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08513287B2
Source datasetuspto-grants-2013_08
ORD IDord-c660bcbccb26410c94989af3ffba5b00
Source noteuspto-grants-2013_08