6-Amino-3-chloropyridazine → 3-Amino-4-bromo-6-chloropyridazine

HRID 1793069Notes

Reaction equation

HRID 1793069 reaction equation
C(=O)(O)[O-].[Na+].[Br:6]Br.[NH2:8][C:9]1[N:10]=[N:11][C:12]([Cl:15])=[CH:13][CH:14]=1>CO>[Br:6][C:14]1[CH:13]=[C:12]([Cl:15])[N:11]=[N:10][C:9]=1[NH2:8]

Participants

5

Reactant 3

HCID 216436-Amino-3-chloropyridazineHCID 24408BromineHCID 516892Sodium Bicarbonate

Product 1

HCID 220244193-Amino-4-bromo-6-chloropyridazineYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium bicarbonate (13.0 g, 155 mmol) and bromine (4.0 mL, 78 mmol) were added to a solution of 3-amino-6-chloropyridazine (10.0 g, 78 mmol) in methanol (150 mL) at room temperature, and the mixture was stirred for 15 hours. The reaction mixture was filtered, and the solvent was evaporated. Water was added thereto, which was extracted with ethyl acetate. The organic layer was washed with a 10% aqueous sodium thiosulfate solution, an aqueous saturated sodium bicarbonate solution and a brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1) to give the title compound (8.6 g, 53%) as tan crystals.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was evaporated
  3. additionWater was added
  4. extractionwhich was extracted with ethyl acetate
  5. washThe organic layer was washed with a 10% aqueous sodium thiosulfate solution
  6. dry with materialan aqueous saturated sodium bicarbonate solution and a brine, dried over anhydrous magnesium sulfate
  7. customevaporated
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1)

Sources & evidence

ORD record
ord-4cc3645b2fc3406b990ff55a9ee5e30d
Source dataset
uspto-grants-2006_07
Patent number
US07078405B2

Reaction notes

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