Triethylamine → 3-hydroxy-4-fluoro-N-cyclopropylbenzamide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide	HCID 15908	—
Reactant	Cyclopropylamine	HCID 69828	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	4-Fluoro-3-hydroxybenzoic acid	HCID 593635	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	3-hydroxy-4-fluoro-N-cyclopropylbenzamide	HCID 22019106	61.5%

Reaction Steps

To a mixture of 3-hydroxy-4-fluorobenzoic acid (1.56 g, 10 mmol), cyclopropylamine (0.6 g, 10.5 mmol), triethylamine (1.02 g, 10 mmol) and HOBt (0.3 g, 2 mol) in DMF (10 mL) was added EDCI (2.0 g, 10.5 mmol) at RT. The mixture was stirred at RT overnight. The mixture was diluted with water and extracted with ethyl acetate (3×20 mL). The extract was washed with water and concentrated to afford 3-hydroxy-4-fluoro-N-cyclopropylbenzamide as a solid (1.2 g, 61.5%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07084160B2
Source dataset	uspto-grants-2006_08
ORD ID	ord-27b9e1260647442584ff0f4565e0531d
Source note	uspto-grants-2006_08