Reaction #336860

ord-b8a2e6cb53f04124b4651771d5d79262

Reaction equation

CCOC(=O)c1cnc2ccc(OC)cc2c1Cl
3d
CCOC(=O)c1cnc2ccc(OC)cc2c1Cl
Ethyl 4-chloro-6-methoxy-quinoline-3-carboxylate
NNc1ccccc1
phenyl hydrazine
→
COc1ccc2[nH]cc3c(=O)n(-c4ccccc4)nc-3c2c1
title compound
COc1ccc2[nH]cc3c(=O)n(-c4ccccc4)nc-3c2c1
8-Methoxy-2-phenyl-2,5-dihydro-pyrazolo-(4,3-c)quinolin-3-one

Reactants

CCOC(=O)c1cnc2ccc(OC)cc2c1Cl
3d
CCOC(=O)c1cnc2ccc(OC)cc2c1Cl
Ethyl 4-chloro-6-methoxy-quinoline-3-carboxylate
NNc1ccccc1
phenyl hydrazine

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

The title compound was prepared following the procedure described in Step 3 using 3d and phenyl hydrazine. 1H NMR (DMSO-d6) δ (ppm): 3.90 (3H, s), 7.17 (1H, m), 7.27 (1H, dd, J=9.06, 2.64 Hz), 7.40 (2H, m), 7.57 (1H, d, J=3.02 Hz), 7.67 (1H, d, J=9.06 Hz), 8.20 (2H, m), 8.63 (1H, s). m/z 292.3 (MH+).

Source

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