1-Chloro-4-(chloromethyl)benzene → HCID 13361806, compound

HRID 2413497Notes

Reaction equation

HRID 2413497 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Cl)=[CH:15][CH:14]=1>C(O)C>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([CH2:17][C:16]3[CH:19]=[CH:20][C:13]([Cl:12])=[CH:14][CH:15]=3)[CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 4597677-Isoquinolinol

Product 1

HCID 13361806HCID 13361806, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.9 g of 7-hydroxyisoquinoline are heated under reflux for 8 hours with 3.5 g of 4-chlorobenzyl chloride in 30 ml of ethanol. After standing overnight, 5.7 g of the isoquinolinium salt crystallize out (melting point: 273°-274°). This salt is dissolved in 200 ml of methanol/water 9:1 and, with cooling, 6 g of sodium borohydride are added. After evolution of hydrogen has ended, the mixture is heated under reflux for 15 minutes. It is then concentrated to 1/3 of its volume, and this is poured into 200 ml of water, ammonium chloride is added to saturation, and the solid material which has precipitated out is filtered off. Recrystallization from ethanol gives 3.6 g of colorless crystals (67% of theory), melting point: 177°-178°.

Workup

  1. custom5.7 g of the isoquinolinium salt crystallize out (melting point: 273°-274°)
  2. dissolutionThis salt is dissolved in 200 ml of methanol/water 9:1
  3. temperaturewith cooling
  4. addition6 g of sodium borohydride are added
  5. temperaturethe mixture is heated
  6. temperatureunder reflux for 15 minutes
  7. concentrationIt is then concentrated to 1/3 of its volume
  8. additionthis is poured into 200 ml of water, ammonium chloride
  9. additionis added to saturation
  10. customthe solid material which has precipitated out
  11. filtrationis filtered off
  12. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-0ba0090ba7e643689c1dd9fa5d7ed352
Source dataset
uspto-grants-1988_01
Patent number
US04717724

Reaction notes

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