Benzyl Bromide → N-benzyl-3-hydroxy-2-phenylpyridinium bromide

HRID 1267876Notes

Reaction equation

HRID 1267876 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:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[Br-:21].[CH2:14]([N+:4]1[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[C:3]=1[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 187052-Phenyl-3-pyridinol

Product 1

HCID 21931695N-benzyl-3-hydroxy-2-phenylpyridinium bromideYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 3-hydroxy-2-phenylpyridine (20 g, 116 mmol) in toluene (250 ml) was heated at reflux for 30 minutes. Benzyl bromide (20 ml) was added and the reaction mixture was heated at reflux for 6 hours then cooled using an ice bath. The solid residue was collected by filtration and washed twice with ether to give crude N-benzyl-3-hydroxy-2-phenylpyridinium bromide (36.5 g, 91%) which was used in the next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 minutes
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for 6 hours
  5. temperaturethen cooled
  6. filtrationThe solid residue was collected by filtration
  7. washwashed twice with ether

Sources & evidence

ORD record
ord-b6e4e5136482453985d2990ab24bf052
Source dataset
uspto-grants-2003_04
Patent number
US06555552B2

Reaction notes

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