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

HRID 858370Notes

Reaction equation

HRID 858370 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-1oneYield 95.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5,6 Dimethoxy indanone (100 grams), Pyridine-4-carboxaldehyde (78.0 grams) and p-toluene sulfonic acid (138.4 grams) were suspended in toluene (1250 ml) and heated to reflux using water separator for 6 hours. The resulting mass was cooled to 25–40° C. and the solid was filtered off under suction. Further the wet solid was suspended in aqueous 10% sodium carbonate solution (1200 ml) and stirred for 30–60 minutes. The resulting pale yellow precipitate solid was filtered off under suction, washed with water (1000 ml) and dried at a temperature of 80° C. to afford 5,6 Dimethoxy-2-(pyridin-4yl)-methylene-indan-1one (Weight: 140 grams, 95.8%).

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. customseparator for 6 hours
  4. temperatureThe resulting mass was cooled to 25–40° C.
  5. filtrationthe solid was filtered off under suction
  6. filtrationThe resulting pale yellow precipitate solid was filtered off under suction
  7. washwashed with water (1000 ml)
  8. customdried at a temperature of 80° C.

Sources & evidence

ORD record
ord-acf7a492bb08448b8618fe9b6060764b
Source dataset
uspto-grants-2006_12
Patent number
US07148354B2

Reaction notes

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