2-Aminopyridine → HCID 178419727, compound

HRID 2233658Notes

Reaction equation

HRID 2233658 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[N+:8]([C:11]1[CH:18]=[CH:17][C:14]([CH2:15][Br:16])=[CH:13][CH:12]=1)([O-:10])=[O:9]>CC#N.CCOCC>[Br-:16].[N+:8]([C:11]1[CH:18]=[CH:17][C:14]([CH2:15][N:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]2=[NH2+:1])=[CH:13][CH:12]=1)([O-:10])=[O:9]

Participants

5

Reactant 2

HCID 104392-AminopyridineHCID 660114-Nitrobenzyl bromide

Product 1

HCID 178419727HCID 178419727, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

1.04 g (11 mmol) of 2-aminopyridine and 2.39 g (11 mmol) of p-nitrobenzylbromide were dissolved in 20 mL CH3CN. The solution was warmed to reflux for 1 hr then cooled to room temperature, diluted with Et2O, and the solid filtered, washed 4× with Et2O and collected to yield 3 g (88%) of 1-(4-Nitro-benzyl)-1H-pyridin-2-ylidene-ammonium bromide (174) as an off white solid.

Workup

  1. temperatureThe solution was warmed
  2. temperatureto reflux for 1 hr
  3. filtrationthe solid filtered
  4. washwashed 4× with Et2O
  5. customcollected

Sources & evidence

ORD record
ord-c134e0a5bac947ffbdb99f177a8da507
Source dataset
uspto-grants-2010_05
Patent number
US07709518B2

Reaction notes

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