Allyl bromide → HCID 22724581, compound

HRID 2088108Notes

Reaction equation

HRID 2088108 reaction equation
[OH:1][C:2]1[C:3]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:14]([Br:17])[CH:15]=[CH2:16]>C1(C)C=CC=CC=1>[Br-:17].[OH:1][C:2]1[C:3]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N+:4]([CH2:16][CH:15]=[CH2:14])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 187052-Phenyl-3-pyridinol

Product 1

HCID 22724581HCID 22724581, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 3-hydroxy-2-phenylpyridine (15 g, 116 mmol) in toluene (250 ml) was heated at reflux for 30 minutes. Allyl bromide (30 ml) was added and the reaction mixture was heated at reflux for 20 hours and cooled using the ice bath. Solid was filtered off and washed twice with ether to afford crude 3-hydroxy-2-phenyl-N-(prop-2-enyl)-pyridinium bromide, which was used treated with acrylonitrile (100 ml), triethylamine (15 ml) and 1,4-dioxane (200 ml) was heated at reflux for 28 hours and cooled to room temperature. The reaction mixture was poured onto saturated aqueous NaHCO3 and extracted with ethyl acetate. The combined organic extracts were dried (Na2SO4) and concentrated to give a crude mixture of regio and stereoisomers in ratio (6R*):(6S*):(7R*):(7S*)=7:8:1:5. Isomers were separated by chromatography on silica gel (iso-hexane:ethyl acetate).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 minutes
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for 20 hours
  5. temperaturecooled
  6. filtrationSolid was filtered off
  7. washwashed twice with ether

Sources & evidence

ORD record
ord-1a35fa4ffb244d05afc8f5a433750c9b
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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