Acetic Acid → HCID 53771658, compound

HRID 1419818Notes

Reaction equation

HRID 1419818 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[F:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.C(O)(=O)C.Cl>C(O)(C)C.CC(C)=O>[F:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[CH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 155921-MethylisoquinolineHCID 680093-Fluorobenzaldehyde

Product 1

HCID 53771658HCID 53771658, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of 6.44 g (0.045 mole) of 1-methylisoquinoline, 6.2 g (0.05 mole) of 3-fluorobenzaldehyde and 18 ml of acetic acid is stirred at a temperature between 130° C. and 140° C. for 3 hours. The termination of the reaction is controlled by thin layer chromatography. The reaction mixture is cooled and 100 ml of anhydrous acetone are added to it. Then it is acidified with a mixture of hydrogen chloride and isopropanol until pH=1 under stirring and cooling with ice-water. The suspension is stirred at a temperature between 0° C. and 5° C. for 2 hours. The separated hydrogen chloride salt is filtered, washed with cold acetone and dissolved in 180 ml of water. To the thus-obtained mixture 20% sodium hydroxide solution is dropped until pH=11-12 under stirring and cooling with ice-water, and the solution is extracted three times with 75 ml each of dichloromethane. The extracts are combined, washed with an aqueous sodium chloride solution, dried over Na2SO4 and evaporated. The crude product is recrystallized from 30 ml of isopropanol. Thus 8.7 g (78%) of 1-(3-fluorostyryl)-isoquinoline are obtained.

Workup

  1. temperatureThe reaction mixture is cooled
  2. stirringunder stirring
  3. stirringThe suspension is stirred at a temperature between 0° C. and 5° C. for 2 hours
  4. filtrationThe separated hydrogen chloride salt is filtered
  5. washwashed with cold acetone
  6. dissolutiondissolved in 180 ml of water
  7. additionTo the thus-obtained mixture 20% sodium hydroxide solution is dropped until pH=11-12
  8. stirringunder stirring
  9. temperaturecooling with ice-water
  10. extractionthe solution is extracted three times with 75 ml each of dichloromethane
  11. washwashed with an aqueous sodium chloride solution
  12. dry with materialdried over Na2SO4
  13. customevaporated
  14. customThe crude product is recrystallized from 30 ml of isopropanol

Sources & evidence

ORD record
ord-8967093799f840bc90862c6cdd26f62e
Source dataset
uspto-grants-1999_03
Patent number
US05889018

Reaction notes

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