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

HRID 2239816Notes

Reaction equation

HRID 2239816 reaction equation
[Br:1]Br.[NH2:3][C:4]1[N:5]=[N:6][C:7]([Cl:10])=[CH:8][CH:9]=1.C(=O)(O)[O-].[Na+]>CO>[NH2:3][C:4]1[N:5]=[N:6][C:7]([Cl:10])=[CH:8][C:9]=1[Br:1]

Participants

5

Reactant 3

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

Product 1

HCID 220244193-Amino-4-bromo-6-chloropyridazineYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Bromine (9.71 g, 3.15 mL, 60.75 mmol) was added dropwise to a mixture of 3-amino-6-chloropyridazine (7.87 g, 60.75 mmol) in methanol (115 mL) and sodium bicarbonate (10.22 g, 121.67 mmol). The resultant mixture was stirred at room temperature for 16 hours and then filtered. Water (500 mL) was added to the filtrate and the solution was extracted with ethyl acetate (3×500 mL). The organic layers were combined and concentrated in vacuo. The resulting residue was purified by flash chromatography eluting with 1/1 hexane/ethyl acetate to give 5.40 g (43%) 3-amino-4-bromo-6-chloropyridazine.

Workup

  1. filtrationfiltered
  2. additionWater (500 mL) was added to the filtrate
  3. extractionthe solution was extracted with ethyl acetate (3×500 mL)
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by flash chromatography
  6. washeluting with 1/1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-9908ac79cd7743cd91d05c56d6ceade9
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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