Thionyl Chloride → (E)-4-(4-chloro-1-butenyl)isoquinoline

HRID 1651109Notes

Reaction equation

HRID 1651109 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](/[CH:11]=[CH:12]/[CH2:13][CH2:14]O)=[CH:3][N:2]=1.S(Cl)([Cl:18])=O>C(Cl)(Cl)Cl>[Cl:18][CH2:14][CH2:13]/[CH:12]=[CH:11]/[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=[N:2][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14750832(E)-4-(4-isoquinolinyl)-3-buten-1-ol

Product 1

HCID 14750833(E)-4-(4-chloro-1-butenyl)isoquinoline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 3.3 g of (E)-4-(4-isoquinolinyl)-3-buten-1-ol in 15 mL of dry chloroform was added to a cold solution of 1.8 mL of thionyl chloride in 5 mL of dry chloroform. After 15 minutes, the cooling bath was removed and the reaction was stirred at room temperature for 1 hour and then at reflux for 3 hours. The cooled mixture was washed with NaHCO3 solution and with brine, then was dried (Na2SO4) and evaporated. The residue was purified by chromatography over silica gel (ethyl acetate-toluene; 3:17) to yield 2.2 g of (E)-4-(4-chloro-1-butenyl)isoquinoline as an oil.

Workup

  1. customthe cooling bath was removed
  2. temperatureat reflux for 3 hours
  3. washThe cooled mixture was washed with NaHCO3 solution and with brine
  4. dry with materialwas dried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by chromatography over silica gel (ethyl acetate-toluene; 3:17)

Sources & evidence

ORD record
ord-2f8f296ba5bf4c39b466f505902ef0ba
Source dataset
uspto-grants-1990_05
Patent number
US04927826

Reaction notes

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