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0 °C

To a solution of 4-cyclobutyl-5-(5-ethoxy-4H-1,2,4-triazol-3-yl)-2-methylbenzamide (219.8, 0.1 g, 0.33 mmol) in TFA (5 ml) was added NaNO2 (0.046 g, 0.66 mmol) at 0° C. The mixture was stirred at 0° C. for 1 hour then at room temperature for 2 hours. The mixture was concentrated under reduced pressure. The residue was partitioned between EtOAc and brine. The aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated to give a clear oil. Yield: 0.1 g, 100%. m/z (ES−) 300 (M−H)−.

1. waitat room temperature for 2 hours
2. concentrationThe mixture was concentrated under reduced pressure
3. customThe residue was partitioned between EtOAc and brine
4. extractionThe aqueous layer was extracted with EtOAc
5. dry with materialThe combined organic layers were dried (Na2SO4)
6. concentrationconcentrated
7. customto give a clear oil