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

HRID 2232147Notes

Reaction equation

HRID 2232147 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-c17e36e5c3004c5485268071b71fdd35
Source dataset
uspto-grants-1988_11
Patent number
US04786646

Reaction notes

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