Reaction #336850

ord-14d96c75fdcb4a85a34f10dc3a1a4f64

Reaction equation

CCOC(=O)c1cnc2ccccc2c1Cl
ethyl 4-chloro-quinoline-3-carboxylate
CCOC(=O)c1cnc2ccccc2c1Cl
Ethyl 4-chloro-quinoline-3-carboxylate
CCN(CC)CC
triethylamine
NNc1ccccc1
phenyl hydrazine
O=c1c2c[nH]c3ccccc3c-2nn1-c1ccccc1
crude product
O=c1c2c[nH]c3ccccc3c-2nn1-c1ccccc1
2-Phenyl-2,5-dihydro-pyrazolo-(4,3-c) quinolin-3-one

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

A suspension of ethyl 4-chloro-quinoline-3-carboxylate (3a) (2.35 g, 0.01 M) in 20 mL of o-xylene was refluxed with triethylamine (2.0 mL, 0.02 M) and phenyl hydrazine (2.89 g, 0.02 M) overnight. The crude product was obtained by filtration followed by washing the solid with cold methanol.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07863266B2uspto-grants-2011_01