Sodium Carbonate → 4-(2-ethylphenyl)-5-methoxy-2-methyl-3(2H)-pyridazinone

HRID 508587Notes

Reaction equation

HRID 508587 reaction equation
Cl[C:2]1[C:3](=[O:11])[N:4]([CH3:10])[N:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH2:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1B(O)O)[CH3:13].C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:2]1[C:3](=[O:11])[N:4]([CH3:10])[N:5]=[CH:6][C:7]=1[O:8][CH3:9])[CH3:13]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27749384-Chloro-5-methoxy-2-methyl-2,3-dihydropyridazin-3-oneHCID 41008622-Ethylphenylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 574373174-(2-ethylphenyl)-5-methoxy-2-methyl-3(2H)-pyridazinoneYield 92%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×

Procedure

To a mixture of 2.516 g of 4-chloro-5-methoxy-2-methyl-3(2H)-pyridazinone, 2.575 g of 2-ethylphenylboronic acid and 3.333 g of sodium carbonate were added 30 mL of 1,4-dioxane and 20 mL of water. To the mixture were added 2.417 g of tetrabutylammonium bromide and 0.657 g of tetrakis(triphenylphosphine)palladium, and then under a nitrogen atmosphere, the resulting mixture was stirred and heated under reflux for 17 hours. After cooling, 50 mL of water was added to the reaction mixture, which was extracted with 100 mL of ethyl acetate and then 30 mL of ethyl acetate. The extracts were combined, washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The solid obtained was washed with a mixed solvent of ethyl acetate and hexane (1:2) to yield 3.238 g of the title compound as yellow crystals.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 17 hours
  3. temperatureAfter cooling
  4. extractionwas extracted with 100 mL of ethyl acetate
  5. washwashed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customThe solid obtained
  9. washwas washed with a mixed solvent of ethyl acetate and hexane (1:2)

Sources & evidence

ORD record
ord-3aa29f9a475447a0b0b1adf0e6cb5ece
Source dataset
uspto-grants-2015_08
Patent number
US09096533B2

Reaction notes

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