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

HRID 2301432

Reaction equation

HRID 2301432 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-1988ac31635f44e0afd9cf754cfd2cda
Source dataset
uspto-grants-2002_12
Patent number
US06500842B1

Linked notes

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