p-Toluenesulfonic acid → HCID 86611641, compound

HRID 1881742Notes

Reaction equation

HRID 1881742 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])[CH:7]([CH2:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)[CH2:6]2.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28]([OH:31])(=[O:30])=[O:29])=[CH:24][CH:23]=1>O=[Pt]=O.CO>[C:22]1([CH3:32])[CH:23]=[CH:24][C:25]([S:28]([OH:31])(=[O:29])=[O:30])=[CH:26][CH:27]=1.[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][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[CH2:6]2

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 100852305,6-Dimethoxy-2-(pyridin-4-ylmethyl)indan-1-one

Product 1

HCID 86611641HCID 86611641, compoundYield 108.8%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

0.60 g of 2,3-dihydro-5,6-dimethoxy-2-((pyridin-4-yl)methyl)inden-1-one, and 0.36 g p-toluenesulfonic acid salt were added to 30 mL of anhydrous methanol. 60 milligrams of PtO2 were added. The reaction mixture was stirred at room temperature, with H2 being added at 1 atmosphere for 6 hours. Solids were filtered off. The filtrate was concentrated and dried in vacuo to afford 1.05 g of foam with 100% yield. Liquid chromatography analysis of this product showed 97% purity.

Workup

  1. additionadded at 1 atmosphere for 6 hours
  2. filtrationSolids were filtered off
  3. concentrationThe filtrate was concentrated
  4. customdried in vacuo

Sources & evidence

ORD record
ord-8cf546c807fe471b9c7c11da39cf39ae
Source dataset
uspto-grants-2012_11
Patent number
US08318942B2

Reaction notes

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