p-Toluenesulfonic acid → 5,6-Dimethoxy-2-(4-pyridyl)methylene-1-indanone

HRID 1645378Notes

Reaction equation

HRID 1645378 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])[CH2:7][CH2:6]2.[N:15]1[CH:20]=[CH:19][C:18]([CH:21]=O)=[CH:17][CH:16]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=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])[C:7](=[CH:21][C:18]1[CH:19]=[CH:20][N:15]=[CH:16][CH:17]=1)[CH2:6]2

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 10340Sodium CarbonateHCID 133894-PyridinecarboxaldehydeHCID 750185,6-Dimethoxy-1-indanone

Product 1

HCID 533951325,6-Dimethoxy-2-(4-pyridyl)methylene-1-indanoneYield 90.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5,6-dimethoxy-indan-1-one (10 g), pyridine-4-carboxaldehyde (7.8 g), p-toluenesulphonic acid (13.8 g) in toluene (120 ml) was refluxed azeotropically for 6 hours. The reaction mixture was cooled to room temperature and filtered. The wet solid so obtained was stirred with 10% aqueous sodium carbonate solution. The solid was filtered, washed with acetone and then dried to get the title compound (13.2 g).

Workup

  1. temperaturewas refluxed azeotropically for 6 hours
  2. filtrationfiltered
  3. customThe wet solid so obtained
  4. filtrationThe solid was filtered
  5. washwashed with acetone
  6. customdried

Sources & evidence

ORD record
ord-2c94bbc0b36a4f348dcc56bbb273af71
Source dataset
uspto-grants-2012_02
Patent number
US08124783B2

Reaction notes

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