1-[2-Chloro-1-hydroxy-3-(6-quinolinyl)propyl]-2,5-pyrrolidinedione Chemical Properties

Boiling point:

598.3±50.0 °C(Predicted)

Density 

1.434±0.06 g/cm3(Predicted)

vapor pressure 

0-0Pa at 20-25℃

pka

11.45±0.20(Predicted)

InChI

InChI=1S/C16H15ClN2O3/c17-12(16(22)19-14(20)5-6-15(19)21)9-10-3-4-13-11(8-10)2-1-7-18-13/h1-4,7-8,12,16,22H,5-6,9H2

InChIKey

FUPWOFWDARMISK-UHFFFAOYSA-N

SMILES

N1(C(O)C(Cl)CC2=CC=C3C(=C2)C=CC=N3)C(=O)CCC1=O

LogP

0.9 at 20℃ and pH7

1-[2-Chloro-1-hydroxy-3-(6-quinolinyl)propyl]-2,5-pyrrolidinedione Usage And Synthesis

Synthesis

A solution of 3-quinolin-6-ylpropanal in acetonitrile was cooled to 0° C before L-proline, benzoic acid, and N-chlorosuccinimide were added at 0° C. The reaction mixture was stirred at 0° C for 3 h, and the resulting clear solution was allowed to warm to room temperature and stirred at RT for 18 h. The reaction mixture became a thick suspension, and LCMS showed the completion of the reaction. Ethyl acetate (EtOAc) was added to the reaction mixture, stirring at room temperature for 1 h. The solids were collected by filtration, washed with ethyl acetate, and dried under vacuum at 40-45° C to constant weight to afford 1-[2-Chloro-1-hydroxy-3-(6-quinolinyl)propyl]-2,5-pyrrolidinedione as an off-white powder. yield: 65.