Pyridine → N-(4-Chlorophenyl)-3-phenylacrylamide

https://huagongshe.com/en/reaction/2080

Participants

Role	Name	HCID	Charge
Reactant	Pyridine	HCID 1049	—
Reactant	4-Chloroaniline	HCID 7812	—
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	3-Phenylprop-2-enoyl chloride	HCID 66023	—
Solvent	Water	HCID 962	—
Solvent	Toluene	HCID 1140	—
Product	N-(4-Chlorophenyl)-3-phenylacrylamide	HCID 303259	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

To a mixture of 4-chloroaniline (16.2 g), toluene (120 ml), and pyridine (11 ml) at 0° C., cinnamoyl chloride (20.0 g) in 120 ml of toluene was added dropwise. After stirring 15 minutes at 0° C. the reaction mixture was poured into a mixture of ethyl acetate: water (250 ml:250 ml). The organic layer was separated and extracted with 5% aqueous HCl (3×250 ml), water (1×250 ml), 5% aqueous sodium bicarbonate (3×250 ml), dried over anhydrous sodium sulfate and yielding the amide as a white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05728694
Source dataset	uspto-grants-1998_03
ORD ID	ord-06bfd03f154d4600bce4486454c4cfc1
Source note	uspto-grants-1998_03