4-Benzylpyridine → HCID 86600924, compound

HRID 902009Notes

Reaction equation

HRID 902009 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:16]=1[S:23]([O:26][NH2:27])(=[O:25])=[O:24]>C(Cl)Cl>[CH3:22][C:17]1[CH:18]=[C:19]([CH3:21])[CH:20]=[C:15]([CH3:14])[C:16]=1[S:23]([O-:26])(=[O:25])=[O:24].[CH2:1]([C:8]1[CH:13]=[CH:12][N:11]([NH3+:27])[CH2:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 164584-BenzylpyridineHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

Product 1

HCID 86600924HCID 86600924, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-benzyl pyridine (0.6 g, 3.5 mmol) in methylene chloride (5 ml) is cooled with ice bath. Freshly prepared O-(2,4,6-trimethyl-benzenesulfonyl)hydroxylamine (0.92 g, 4.2 mmol) in methylene chloride (5 ml) is added dropwise with stirring. The ice bath is removed and the mixture stirred for 1 hour, then concentrated in vacuo. The residue is dissolved in methylene chloride and precipitated with hexanes. The hexane layer is decanted. Concentration provides 1.0 g (62%) of the title compound as a viscous oil.

Workup

  1. customThe ice bath is removed
  2. stirringthe mixture stirred for 1 hour
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue is dissolved in methylene chloride
  5. customprecipitated with hexanes
  6. customThe hexane layer is decanted
  7. concentrationConcentration

Sources & evidence

ORD record
ord-2b021d9745f045649e721c4701e7cc4c
Source dataset
uspto-grants-2008_04
Patent number
US07365066B2

Reaction notes

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