Methanol → 5,6-Dimethoxy-2-(pyridin-4-ylmethyl)indan-1-one

HRID 269382Notes

Reaction equation

HRID 269382 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[C:7](=[CH:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)[CH2:6]2.CO.C(Cl)Cl>[Pd].C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[CH:7]([CH2:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)[CH2:6]2

Participants

6

Reactant 3

HCID 887MethanolHCID 6344DichloromethaneHCID 533951325,6-Dimethoxy-2-(4-pyridyl)methylene-1-indanone

Product 1

HCID 100852305,6-Dimethoxy-2-(pyridin-4-ylmethyl)indan-1-oneYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

The mixture of 5,6-dimethoxy-2-(4-pyridyl)methylene-1-indanone (34 gm), methanol (325 ml), methylenedichloride (200 ml) and 5% palladium-charcoal (2 gm) is taken in a hydrogenation flask and subjected to hydrogenation under a hydrogen pressure of 2 bars for 3 hours. The catalyst is removed by filtration and the solvents are evaporated completely under vacuum to obtain a residue. Ethyl acetate (150 ml) is added to the residue and stirred for 20 minutes at 25° C. to 30° C. The contents are then cooled to 0° C., stirred for 30 minutes and filtered to give 34 gm of 5,6-dimethoxy-2-(4-pyridyl)methyl-1-indanone.

Workup

  1. customis taken in a hydrogenation flask
  2. customfor 3 hours
  3. customThe catalyst is removed by filtration
  4. customthe solvents are evaporated completely under vacuum
  5. customto obtain a residue
  6. stirringstirred for 30 minutes
  7. filtrationfiltered

Sources & evidence

ORD record
ord-c60d37808dc2482281bba3c17a9b3fe5
Source dataset
uspto-grants-2008_11
Patent number
US07446203B2

Reaction notes

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