Ammonium Chloride → 6-Bromo-4-methylpyridin-3-amine

HRID 59940

Reaction equation

HRID 59940 reaction equation
[NH4+].[Cl-].[Br:3][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([N+:11]([O-])=O)=[CH:6][N:5]=1>O.[Fe]>[Br:3][C:4]1[N:5]=[CH:6][C:7]([NH2:11])=[C:8]([CH3:10])[CH:9]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 3458732-Bromo-4-methyl-5-nitropyridine

Product 1

HCID 199260946-Bromo-4-methylpyridin-3-amine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of NH4Cl (14.9 mmol) and iron powder (18.4 mmol) in H2O (5 mL) was stirred at 90° C. 2-bromo-4-methyl-5-nitropyridine (2.3 mmol) was added in portions. The mixture was stirred at 90° C. for 1 h and 15 min. The reaction was stopped and extracted with EtOAc. The organic layer was dried (Na2SO4) and concentrated to yield the desired product.

Workup

  1. stirringThe mixture was stirred at 90° C. for 1 h and 15 min
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-25b06232104b4fb280ad8f917456b77e
Source dataset
uspto-grants-2016_09
Patent number
US09440929B2

Linked notes

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