HCID 22734278, compound → HCID 22734005, compound

HRID 2084793Notes

Reaction equation

HRID 2084793 reaction equation
Cl[C:2]1[CH:3]=[N:4][CH:5]=[C:6](Cl)[C:7]=1[CH2:8][C:9]([C:11]1[C:20]2[O:19][CH2:18][CH2:17][O:16][C:15]=2[C:14]([O:21][CH3:22])=[CH:13][CH:12]=1)=[O:10].[H][H]>CN(C=O)C.[C].[Pd]>[CH3:22][O:21][C:14]1[C:15]2[O:16][CH2:17][CH2:18][O:19][C:20]=2[C:11]([C:9](=[O:10])[CH2:8][C:7]2[CH:6]=[CH:5][N:4]=[CH:3][CH:2]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 22734278HCID 22734278, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22734005HCID 22734005, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

Compound 178 (1.1 g) obtained in Example 178 was dissolved in DMF (10 ml), mixed with palladium carbon (containing 50% water) (0.2 g), and stirred at room temperature for 24 hours in a hydrogen atmosphere. The reaction solution was filtered with Celite. The filtrate was mixed with saturated sodium bicarbonate water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate anhydride, and evaporated under reduced pressure for removing the solvent. The residue was purified by silica gel column chromatography (ethyl acetate) to give 2,3-dihydro-5-methoxy-8-[1-oxo-2-(4-pyridyl)ethyl]-1,4-benzodioxine (0.36 g, 41%) as colorless crystals. The thus-obtained compound was dissolved in ethyl acetate and mixed with a saturated hydrochloric acid ethyl acetate solution. The precipitated crystals were filtered and washed with ethyl acetate to give Compound 179 as colorless crystals.

Workup

  1. filtrationThe reaction solution was filtered with Celite
  2. additionThe filtrate was mixed with saturated sodium bicarbonate water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate anhydride
  6. customevaporated under reduced pressure
  7. customfor removing the solvent
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-b5be4b16c4454f7facb6aaa58c2bf1f4
Source dataset
uspto-grants-2004_04
Patent number
US06716987B1

Reaction notes

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