Ammonium Chloride → N2-(tert-Butyl)pyridine-2,3-diamine

HRID 253966Notes

Reaction equation

HRID 253966 reaction equation
[C:1]([NH:5][C:6]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-]>CO.[Zn]>[C:1]([NH:5][C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][N:7]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 601972N-tert-butyl-3-nitropyridin-2-amine

Product 1

HCID 15656135N2-(tert-Butyl)pyridine-2,3-diamine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a solution of the N-tert-butyl-3-nitropyridin-2-amine in MeOH (200 mL), was added solid NH4Cl (16.4 g, 306.54 mmol) and zinc dust (10.0 g, 153 mmol). The suspension was heated under reflux for 3 hours and then cooled to RT. After filtration through Celite™, the solvent was removed by vacuum evaporation. The resulting black residue was taken up to EtOAc (300 mL) and filtered through Celite™ again to remove the remaining NH4Cl. The solvent was again evaporated and the residue was dried on the high vacuum oil pump overnight to yield N2-tert-butylpyridine-2,3-diamine.

Workup

  1. temperatureThe suspension was heated
  2. temperatureunder reflux for 3 hours
  3. filtrationAfter filtration through Celite™
  4. customthe solvent was removed by vacuum evaporation
  5. filtrationfiltered through Celite™ again
  6. customto remove the remaining NH4Cl
  7. customThe solvent was again evaporated
  8. customthe residue was dried on the high vacuum oil

Sources & evidence

ORD record
ord-04b3a85d442743fc9871b5eec0ee4df5
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

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