Bromine → 5-Amino-6-bromo-3-chloro-2-pyridinecarbonitrile

HRID 1622083Notes

Reaction equation

HRID 1622083 reaction equation
[Br:1]Br.[NH2:3][C:4]1[CH:5]=[C:6]([Cl:12])[C:7]([C:10]#[N:11])=[N:8][CH:9]=1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[NH2:3][C:4]1[CH:5]=[C:6]([Cl:12])[C:7]([C:10]#[N:11])=[N:8][C:9]=1[Br:1]

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 218750995-Amino-3-chloropyridine-2-carbonitrile

Product 1

HCID 865884815-Amino-6-bromo-3-chloro-2-pyridinecarbonitrileYield 89.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

Bromine (7.22 g) was added to a stirring mixture of 5-amino-3-chloro-2-cyanopyridine (4.61 g) and sodium acetate (4.81 g) in anhydrous acetic acid (150 mL) at room temperature. The mixture was stirred at 60° C. for 2 hours. The solvents and excess bromine were evaporated and the residue was recrystallized from ethyl acetate to give 5-amino-6-bromo-3-chloro-2-cyano-pyridine (6.23 g).

Workup

  1. customThe solvents and excess bromine were evaporated
  2. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-511306f0b06f4de09f9a30e72d706613
Source dataset
uspto-grants-2014_07
Patent number
US08778625B2

Reaction notes

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