Acetic Acid → HCID 86720741, compound

HRID 512932Notes

Reaction equation

HRID 512932 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

5

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 100173053-[(E)-2-(7-Chloroquinolin-2-yl)ethenyl]benzaldehydeHCID 22559816Acetone tetrahydrofuran

Product 1

HCID 86720741HCID 86720741, compoundYield 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.

Workup

  1. customThe reaction mixture was evaporated to half volume
  2. additionpoured into water (200 ml)
  3. customThe solid separated out
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-cbe1d4cd1c0044bc8dea177f2dc47c06
Source dataset
uspto-grants-2015_08
Patent number
US09102665B2

Reaction notes

Loading…