Hydrochloric Acid → 8-(3-(1-(4-Chlorophenyl)-2-(pyridin-4-yl)ethyl)phenyl)-6-isopropylquinoline

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Sodium Hydroxide	HCID 14798	—
Reactant	3-(4-Chloro-phenyl)-3-[3-(6-isopropyl-quinolin-8-yl)-phenyl]-2-pyridin-4-yl-propionic acid ethyl ester	HCID 20814966	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	Tetrahydrofuran ethanol	HCID 21873804	—
Product	8-(3-(1-(4-Chlorophenyl)-2-(pyridin-4-yl)ethyl)phenyl)-6-isopropylquinoline	HCID 10183196	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

To a solution of the crude ester from Step 3 above in THF/EtOH (10 mL) was added NaOH (2N, 2 mL). The resulting reaction mixture was stirred 18 h at 100° C. then neutralized with HCl 6N to pH 7 and diluted with ethyl acetate. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (eluting with hexane/ethyl acetate, 1:1) provided the 8-{3-[1-(4-chloro-phenyl)-2-pyridin-4-yl-ethyl]-phenyl}-6-isopropyl-quinoline compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06919353B2
Source dataset	uspto-grants-2005_07
ORD ID	ord-18cb4c5d5fee4d0991dae9e76022921f
Source note	uspto-grants-2005_07