Acetic Acid → (E)-4-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-but-3-en-2-one

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=3)[CH:17]=O)=[N:9]2)=[CH:4][CH:3]=1.[OH-].[Na+].C(O)(=O)C.[CH3:28][C:29]([CH3:31])=[O:30].C1COCC1>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16](/[CH:17]=[CH:28]/[C:29](=[O:30])[CH3:31])[CH:19]=[CH:20][CH:21]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 176Acetic Acid

HCID 14798Sodium Hydroxide

HCID 100173053-[(E)-2-(7-Chloroquinolin-2-yl)ethenyl]benzaldehyde

HCID 22559816Acetone tetrahydrofuran

Product 1

HCID 86720741(E)-4-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-but-3-en-2-oneYield 76.47%

Procedure

To a solution of aldehyde 29 (15 g, 0.0519 mol) in a mixture of 200 ml of Acetone:THF (1:1) was added 10% aq. NaOH solution and stirred for 3 hours. Dilute acetic acid was added till pH of mixture was acidic. The reaction mixture was evaporated to half volume and poured into water (200 ml). The solid separated out was filtered to yield (E)-4-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-but-3-en-2-one (13 g, 76.47%) as a yellow solid.