1,2,3,4-Tetrahydroisoquinoline → 3,4-Dihydroisoquinoline

HRID 1723467Notes

Reaction equation

HRID 1723467 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.[S]>C1(C)C=CC=CC=1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]=1

Participants

4

Reactant 2

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 5362487Sulfur2×

Product 1

HCID 767053,4-DihydroisoquinolineYield 93.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

30.0 g of 1,2,3,4-tetrahydroisoquinoline and 15.0 g of sulphur powder in 200 ml of toluene are refluxed for 7 hours. After cooling the sulphur is filtered off, the filtrate is evaporated in vacuo. The resulting thick oily residue is distilled in vacuo. 27.5 g of 3,4-dihydroisoquinoline are obtained, b.p. 64°-67° C. at 0.6 mmHg.

Workup

  1. filtrationis filtered off
  2. customthe filtrate is evaporated in vacuo
  3. distillationThe resulting thick oily residue is distilled in vacuo

Sources & evidence

ORD record
ord-6234181c243343e593863b276e6b7280
Source dataset
uspto-grants-1989_08
Patent number
US04861888

Reaction notes

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