Chloride 2-chloropyridinium 1-oxide → HCID 22118704, compound

HRID 1274982Notes

Reaction equation

HRID 1274982 reaction equation
[C:1]([N:8]([CH3:12])[CH2:9][CH2:10][NH2:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.Cl[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N+:16]=1[O-].C([O-])(O)=O.[Na+]>C(O)(CC)(C)C.CCO>[C:1]([N:8]([CH3:12])[CH2:9][CH2:10][NH:11][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

6

Reactant 3

HCID 88478Chloride 2-chloropyridinium 1-oxideHCID 516892Sodium BicarbonateHCID 2756424N-Boc-N-methylethylenediamine

Product 1

HCID 22118704HCID 22118704, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 64052-Methyl-2-butanolSolvent

Procedure

A mixture of N-Boc-N-(methyl)ethylenediamine (Synth. Commun. 1993, 23, 2443-2449)(849.2 mg, 4.87 mmol), 2-chloropyridine N-oxide hydrochloride (970 mg, 5.84 mmol), and NaHCO3 (2.05 g, 24.4 mmol) in tert-amyl alcohol (12 mL) was heated at reflux under argon. After 41.5 h, the reaction was cooled, diluted with EtOH, filtered, and concentrated. The residue was reconcentrated from toluene and chromatographed (silica gel, 5% CH3OH/CHCl3) to give the title compound as a viscous, yellow oil which was used without further purification (863.1 mg, 66%), MS (ES) m/e 268 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under argon
  3. temperaturethe reaction was cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed (silica gel, 5% CH3OH/CHCl3)

Sources & evidence

ORD record
ord-1e413e5995a74e699800086e8519890d
Source dataset
uspto-grants-2000_12
Patent number
US06159964

Reaction notes

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