HCID 22176515, compound → 2-Bromo-6-methylpyridin-4-amine

HRID 965877Notes

Reaction equation

HRID 965877 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([CH2:11]C)[N+:3]=1[O-]>C(O)(=O)C.[Fe]>[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([CH3:11])[N:3]=1

Participants

4

Reactant 1

HCID 22176515HCID 22176515, compound

Product 1

HCID 126437102-Bromo-6-methylpyridin-4-amine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2-bromo-6-ethyl-4-nitro-pyridine 1-oxide (15.9 g, 69 mmol) in acetic acid (310 ml) was treated with powdered iron (25.8 g, 462 mmol). The mixture was slowly heated to 100° C. and kept for 1 hr. Then the reaction mixture was cooled to rt and filtered. After evaporation of the solvent the residue was crystallized to yield the title compound as a beige material (88%). Mp. 75-77° C. (pentane), MS: m/e=200 (M+).

Workup

  1. temperatureThen the reaction mixture was cooled to rt
  2. filtrationfiltered
  3. customAfter evaporation of the solvent the residue
  4. customwas crystallized

Sources & evidence

ORD record
ord-1a3416907eb24c63b9b810d2fb40b780
Source dataset
uspto-grants-2005_10
Patent number
US06951875B2

Reaction notes

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