4-Aminophenol → N-(4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

https://huagongshe.com/reaction/520662

Participants

Role	Name	HCID	Charge
Reactant	4-Aminophenol	HCID 403	—
Reactant	1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide	HCID 15908	—
Reactant	HOAt	HCID 181649	—
Reactant	Antipyric acid	HCID 246564	—
Solvent	Water	HCID 962	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	N-(4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide	HCID 90032700	52.6%

Reaction Conditions

Temperature	46 °C

Reaction Steps

To a mixture of 4-aminophenol (1.09 g, 10 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (2.37 g, 10.2 mmol) in DCM (30 mL) was added EDCI (2.3 g, 12 mmol) and HOAT (0.27 g, 2 mmol). The mixture was stirred at 46° C. for 4 hours, then cooled to rt and diluted with EtOAc (10 mL) and water (10 mL). The mixture was stirred at rt for 1 hour, then filtered to give the title compound as a white solid (1.7 g, 52.5%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09326975B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-7e336b959bf24b3184b22fca555ec71d
Source note	uspto-grants-2016_05