Sodium Hydroxide → 5-Amino-6-bromo-2-pyridinecarbonitrile

HRID 400574

Reaction equation

HRID 400574 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[Br:10]Br.[OH-].[Na+]>C(O)(=O)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][C:7]=1[Br:10]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 38713955-Aminopyridine-2-carbonitrile

Product 1

HCID 242138925-Amino-6-bromo-2-pyridinecarbonitrileYield 35.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

5-Aminopyridine-2-carbonitrile (2.38 g, 20 mmol) was dissolved in 6 mL of glacial acetic acid. A solution of bromine (1 mL, 20 mmol) in 2.5 mL of glacial acetic acid was added dropwise over a period of 30 minutes while the room temperature was maintained with a water bath. The resulting slurry was stirred for 1 hour at room temperature, treated with 50 mL of aqueous 20% sodium hydroxide solution and extracted with three 160 mL portions of dichloromethane. The combined organic layers were dried over sodium sulfate (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by crystallization from ethyl acetate-hexanes to give 5-amino-6-bromopyridine-2-carbonitrile (1.42 g, 35% yield).

Workup

  1. temperaturewas maintained with a water bath
  2. extractionextracted with three 160 mL portions of dichloromethane
  3. dry with materialThe combined organic layers were dried over sodium sulfate (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by crystallization from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-3f12eec8677b4ebf8019de91e1881cd1
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Linked notes

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