Benzaldehyde → 2-(2-Phenylethenyl)-8-Quinolinol

HRID 323000Notes

Reaction equation

HRID 323000 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[C:14]1([CH:13]=[CH:12][C:9]2[CH:8]=[CH:7][C:6]3[C:11](=[C:2]([OH:1])[CH:3]=[CH:4][CH:5]=3)[N:10]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 240BenzaldehydeHCID 132242-Methyl-8-hydroxyquinoline

Product 1

HCID 4698252-(2-Phenylethenyl)-8-Quinolinol

Procedure

A mixture of 8-hydroxyquinaldine (10.02 g) and benzaldehyde (16.8 mL) is heated at reflux overnight. The reaction is cooled to room temperature and vacuum distilled. After the excess benzaldehyde has distilled off, the residue remaining in the flask is dissolved in hot 95% EtOH. Any undissolved material is filtered off. The EtOH filtrate is cooled slowly to give the product as light yellow crystals (5.17 g).

Workup

  1. temperatureis heated
  2. temperatureat reflux overnight
  3. distillationvacuum distilled
  4. distillationAfter the excess benzaldehyde has distilled off
  5. dissolutionis dissolved in hot 95% EtOH
  6. filtrationAny undissolved material is filtered off
  7. temperatureThe EtOH filtrate is cooled slowly

Sources & evidence

ORD record
ord-6692eae8dc0d46088b1836a8db893676
Source dataset
uspto-grants-2001_04
Patent number
US06211376B1

Reaction notes

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