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

HRID 1645380
Notes
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Reaction equation

HRID 1645380 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.Cl(O)(=O)(=O)=O>CO.ClCCl.[Pd]>[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 24247Perchloric AcidHCID 533951325,6-Dimethoxy-2-(4-pyridyl)methylene-1-indanone

Product 1

HCID 100852305,6-Dimethoxy-2-(pyridin-4-ylmethyl)indan-1-one

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent
HCID 6344
Dichloromethane
Solvent

Procedure

4-[(5,6-Dimethoxy-1-indanon-2-ylidene)methyl]pyridine (50 g) in methanol and dichloromethane (1:1) was hydrogenated in presence of palladium on carbon (5 g) and a catalytic quantity of perchloric acid at 0.5 kg pressure and room temperature. The solvents were evaporated under vacuum and the residue was taken in ethyl acetate (500 ml), washed with water (50 ml), brine (50 ml), dried over anhydrous sodium sulphate and evaporated in vacuum to yield the product. Yield: 49 g.

Workup

  1. customat 0.5 kg pressure and room temperature
  2. customThe solvents were evaporated under vacuum
  3. washwashed with water (50 ml), brine (50 ml)
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated in vacuum
  6. customto yield the product

Sources & evidence

ORD record
ord-404de8b9b4704b9091687f65c4017a9a
Source dataset
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08124783B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes