1,4-Dioxane → Butyl 3-(2-{[4-(methyloxy)phenyl]methyl}-3,6-dioxo-1,2,3,6-tetrahydro-4-pyridazinyl)propanoate

HRID 2233199Notes

Reaction equation

HRID 2233199 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[C:15](=[O:16])[C:14](/[CH:17]=[CH:18]/[C:19]([O:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:20])=[CH:13][C:12]([O:26]CC3C=CC(OC)=CC=3)=[N:11]2)=[CH:5][CH:4]=1.O1CCOCC1>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[C:15](=[O:16])[C:14]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:20])=[CH:13][C:12](=[O:26])[NH:11]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 68553396butyl (2E)-3-[2-{[4-(methyloxy)phenyl]methyl}-6-({[4-(methyloxy)phenyl]methyl}oxy)-3-oxo-2,3-dihydro-4-pyridazinyl]-2-propenoate

Product 1

HCID 67527033Butyl 3-(2-{[4-(methyloxy)phenyl]methyl}-3,6-dioxo-1,2,3,6-tetrahydro-4-pyridazinyl)propanoateYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of butyl (2E)-3-[2-{[4-(methyloxy)phenyl]methyl}-6-({[4-(methyloxy)phenyl]methyl}oxy)-3-oxo-2,3-dihydro-4-pyridazinyl]-2-propenoate) (838 mg) in ethanol (15 ml)/1,4-dioxane (10 ml) was treated with 10% Pd/C (400 mg) and stirred under hydrogen at atmospheric pressure and RT for 2 hours. The catalyst was filtered off using kieselguhr and the filtrate was evaporated and redissolved in 1,4-dioxane and the solution evaporated to dryness to give the product as a colourless oil (0.56 g, 89%).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. dissolutionredissolved in 1,4-dioxane
  4. customthe solution evaporated to dryness

Sources & evidence

ORD record
ord-4694924d82dd40af8825cacd1cac93c5
Source dataset
uspto-grants-2010_05
Patent number
US07709483B2

Reaction notes

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