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

HRID 1244033Notes

Reaction equation

HRID 1244033 reaction equation
[C:1]1([C:7]2[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:14]([Br:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(#N)C>[Br-:21].[C:15]1([CH2:14][N+:8]2[CH:9]=[CH:10][CH:11]=[C:12]([OH:13])[C:7]=2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[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 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a flame dried round bottom flask equipped with a nitrogen inlet and a condenser was introduced 1.3 gm. (7.59 mmol) 2-phenyl-3-hydroxypyridine, 3.25 gm. 2.26 ml (18.96 mmol) benzylbromide. The contents were dissolved in 30 ml of acetonitrile and the reaction mixture was heated under reflux for a period of 18 hours. The mixture was allowed to cool to room temperature and evaporated in vacuo. The residue was taken up in chloroform followed by treatment with ether to afford a solid precipitate. Upon filtration there was obtained 2.09 gm (81%) of 1-phenylmethyl-2-phenyl-3-hydroxypyridinium bromide. 1H NMR (CDCl3, 400 MHz) δ 8.70 (d, 1H), 8.25 (d, 1H), 7.50 (m, 2H), 7.40 (m, 2H), 7.30–7.20 (m, 5H), 6.90 (d, 2H), 5.60 (s, 2H) ppm. Mass spectrum APCI m/z 262.

Workup

  1. customTo a flame dried round bottom flask
  2. customequipped with a nitrogen inlet and a condenser
  3. additionwas introduced 1.3 gm
  4. temperaturethe reaction mixture was heated
  5. temperatureunder reflux for a period of 18 hours
  6. customevaporated in vacuo
  7. customto afford a solid precipitate
  8. filtrationUpon filtration there

Sources & evidence

ORD record
ord-a7e3733319204d82b8adb7f8cede197c
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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