Water → 5,6 Dimethoxy-2-(pyridin-4yl)-methylene-indan-1one

HRID 1452033Notes

Reaction equation

HRID 1452033 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.O>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])[CH:21]([C:18]1[CH:17]=[CH:16][N:15]=[CH:20][CH:19]=1)[C:6]2=[CH2:7]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 133894-PyridinecarboxaldehydeHCID 750185,6-Dimethoxy-1-indanone

Product 1

HCID 669100075,6 Dimethoxy-2-(pyridin-4yl)-methylene-indan-1one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

##STR6## 19.2 g of 5,6-dimethoxyindanone, 15 g of pyridine-4-aldehyde and 19 g of p-toluenesulphonic acid were heated to boiling under reflux in a water separator for 5 h in 250 ml of toluene. The resulting precipitate was filtered off with suction after cooling and stirred at room temperature for 30 min in 10% strength sodium carbonate solution. The resulting pale-yellow precipitate was filtered off with suction, washed with water and dried in air. Yield: 24.4 g (87%).

Workup

  1. filtrationThe resulting precipitate was filtered off with suction
  2. temperatureafter cooling
  3. filtrationThe resulting pale-yellow precipitate was filtered off with suction
  4. washwashed with water
  5. customdried in air

Sources & evidence

ORD record
ord-526da5b85c2841e6afe09fe0ef94e77f
Source dataset
uspto-grants-1997_02
Patent number
US05606064

Reaction notes

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