Ethanol → 3-Pyridazinamine, 6-chloro-4-(2,4-dimethylphenyl)-

HRID 500992Notes

Reaction equation

HRID 500992 reaction equation
[CH2:1](O)[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[NH2:10][C:11]1[N:12]=[N:13][C:14]([Cl:18])=[CH:15][C:16]=1Br.O.[C:20]1([CH3:26])[CH:25]=C[CH:23]=[CH:22][CH:21]=1>>[Cl:18][C:14]1[N:13]=[N:12][C:11]([NH2:10])=[C:16]([C:23]2[CH:22]=[CH:21][C:20]([CH3:26])=[CH:25][C:1]=2[CH3:2])[CH:15]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 1140TolueneHCID 10340Sodium CarbonateHCID 220244193-Amino-4-bromo-6-chloropyridazine

Product 1

HCID 220244923-Pyridazinamine, 6-chloro-4-(2,4-dimethylphenyl)-Yield 82%

Conditions

Temperature
100 °C

Procedure

Ethanol (8 mL), a 2M aqueous sodium carbonate solution (4 mL), 2,4-dimethylbenzeneboric acid (650 mg, 4.3 mmol) and tetrakistriphenylphosphine palladium complex (456 mg, 0.39 mmol) were added to a solution of 3-amino-4-bromo-6-chloropyridazine (822 mg, 3.9 mmol) in toluene (40 mL), and the mixture was heated at 100° C. for 2 hours. Water was added thereto, which was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3) to give the title compound (759 mg, 82%) as a pale brown powder.

Workup

  1. extractionwhich was extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous saturated sodium bicarbonate solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3)

Sources & evidence

ORD record
ord-af2ebe813cea4c79b1d50497cf48ef51
Source dataset
uspto-grants-2010_08
Patent number
US07772249B2

Reaction notes

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