Hydrochloric Acid → HCID 15354666, compound

HRID 2096522Notes

Reaction equation

HRID 2096522 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[CH:12](=O)[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.[OH-].[Na+].Cl>CCO.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])/[CH:9]=[CH:12]/[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 133894-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 15354666HCID 15354666, compoundYield 42.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

To a solution of 1-(5-bromo-2-hydroxyphenyl)ethanone (50 g, 0.23 mol) in EtOH (285 mL) and H2O (15 mL) was added isonicotinaldehyde (25 g, 0.23 mol) and NaOH (84 g, 0.23 mol). The reaction mixture was stirred overnight. EtOH was added to the mixture and filtered to give a solid residue. The residue was dissolved in water and acidified by 1 M HCl to give a solid. The solid was collected by filtration to give (E)-1-(5-bromo-2-hydroxyphenyl)-3-(pyridin-4-yl)prop-2-en-1-one (30 g, 40%).

Workup

  1. filtrationfiltered
  2. customto give a solid residue
  3. customto give a solid
  4. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-5a7100d42fea4295a0ba806139c0986a
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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