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A mixture of ethyl 5-hydroxy-1-(naphthalen-1-yl)-1H-pyrazole-4-carboxylate (480 mg, 1.8 mmol), aqueous potassium hydroxide solution (35%, 2.2 mL, 13.5 mmol) and methanol (5 mL) was heated to reflux for 24 hours. The reaction mixture was then cooled to 0° C., acidified to pH 2 with conc. HCl and refluxed for additional 12 hours to complete decarboxylation. The reaction was then cooled to room temperature and concentrated. The residue was taken up in water and extracted with ethyl acetate, the organic layer washed with water, dried over sodium sulfate and concentrated. Purification by preparative TLC (95% dichloromethane/5% methanol) afforded 1-(naphthalen-1-yl)-1H-pyrazol-5-ol.

1. temperaturewas heated
2. temperatureto reflux for 24 hours
3. temperaturerefluxed for additional 12 hours
4. temperatureThe reaction was then cooled to room temperature
5. concentrationconcentrated
6. extractionextracted with ethyl acetate
7. washthe organic layer washed with water
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated
10. customPurification by preparative TLC (95% dichloromethane/5% methanol)