Sodium Hydroxide → 2,6-Dibromopyridin-4-amine

HRID 583121Notes

Reaction equation

HRID 583121 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([Br:10])[N+:7]([O-])=[C:6]([Br:12])[CH:5]=1)([O-])=O.[OH-].[Na+]>[Fe].C(O)(=O)C>[NH2:1][C:4]1[CH:9]=[C:8]([Br:10])[N:7]=[C:6]([Br:12])[CH:5]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 110228822,6-Dibromo-4-nitro-1-oxo-1lambda~5~-pyridine

Product 1

HCID 140910412,6-Dibromopyridin-4-amine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-nitro-2,6-dibromopyridine-N-oxide (1.2 g), iron powder (1.2 g) and acetic acid (15 ml) were stirred and heated to 100° C. for 1 hour. Upon cooling the mixture was basified with 3 molar sodium hydroxide and continuously extracted with ether. Removal of the ether under reduced pressure left a white crystalline product of 4-amino-2,6-dibromopyridine (1.0 g, 99%), m.p. 212-214° C.

Workup

  1. temperatureUpon cooling the mixture
  2. extractioncontinuously extracted with ether
  3. customRemoval of the ether under reduced pressure
  4. waitleft a white crystalline product of 4-amino-2,6-dibromopyridine (1.0 g, 99%), m.p. 212-214° C.

Sources & evidence

ORD record
ord-41d7335c703e4c28a2880f228861a85a
Source dataset
uspto-grants-1999_07
Patent number
US05929082

Reaction notes

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