Ammonia → HCID 23388399, compound

To a solution of 1,1′-carbonyldiimidazole (3.4 g, 21 mmol) in 60 mL of dry THF was added dropwise a solution of 1-phenyl-1H-indazole-3-carboxylic acid (5.0 g, 21 mmol) in 60 mL dry THF under nitrogen atmosphere. The resulting reaction mixture was stirred at ambient temperature for 30 minutes and refluxed for 30 minutes; then cooled to ambient temperature under nitrogen atmosphere. Ammonia, generated by warming concentrated aqueous ammonia solution, was bubbled through, and the reaction mixture was stirred overnight at ambient temperature. The reaction mixture was concentrated in vacuo to dryness, the solid was dissolved in 200 mL of ethyl acetate, the solution was successively washed with 1N aqueous HCl solution (2×50 mL), 1N aqueous NaOH solution (5×20 mL) and was dried over Na2SO4. Concentration and drying under vacuum gave 4.65 g (93%) of desired product as a white solid: mp 149° C.

1. customThe resulting reaction mixture
2. temperaturerefluxed for 30 minutes
3. temperaturethen cooled to ambient temperature under nitrogen atmosphere
4. customwas bubbled through, and the reaction mixture
5. stirringwas stirred overnight at ambient temperature
6. concentrationThe reaction mixture was concentrated in vacuo to dryness
7. dissolutionthe solid was dissolved in 200 mL of ethyl acetate
8. washthe solution was successively washed with 1N aqueous HCl solution (2×50 mL), 1N aqueous NaOH solution (5×20 mL)
9. dry with materialwas dried over Na2SO4
10. concentrationConcentration
11. customdrying under vacuum

ORD record

ord-04a10af7cb374fbe971c195a3a836099

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06458781B1