HCID 117693409, compound → HCID 117690823, compound

HRID 1503212Notes

Reaction equation

HRID 1503212 reaction equation
[N:1]1[C:6]2[O:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[O:10][C:5]=2[CH:4]=[C:3](/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:2]=1>C(O)(=O)C.[C].[Pd]>[N:1]1[C:6]2[O:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[O:10][C:5]=2[CH:4]=[C:3]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:2]=1

Participants

4

Reactant 1

HCID 117693409HCID 117693409, compound

Product 1

HCID 117690823HCID 117690823, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution (20 ml) of ethyl (2E)-3-([1,4]benzodioxino[2,3-c]pyridazin-3-yl)acrylate (649 mg) in acetic acid was added 10% palladium-carbon (100 mg), and the mixture was stirred at room temperature for 7 days under a hydrogen atmosphere. The catalyst was filtered off through celite, and the filtrate was concentrated under reduced pressure. To the residue was added saturated aqueous sodium hydrogen carbonate solution and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure to give ethyl 3-([1,4]benzodioxino[2,3-c]pyridazin-3-yl)propanoate (609 mg).

Workup

  1. filtrationThe catalyst was filtered off through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the residue was added saturated aqueous sodium hydrogen carbonate solution
  4. extractionthe mixture was extracted with chloroform
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationthe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3f6d009ed79d4072b088f2ac0c76e5ea
Source dataset
uspto-grants-2015_12
Patent number
US09212147B2

Reaction notes

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