Diphenyl disulfide → 1-(4-Chlorophenyl)-5-methylisoquinoline

HRID 1156863Notes

Reaction equation

HRID 1156863 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[C:13]([CH3:18])[CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][N:9]=2)=[CH:4][CH:3]=1.C1(SSC2C=CC=CC=2)C=CC=CC=1>C1C2C(=CC=CC=2)CCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[C:13]([CH3:18])[CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 13436Diphenyl disulfideHCID 128518201-(4-Chlorophenyl)-5-methyl-3,4-dihydroisoquinoline

Product 1

HCID 128518261-(4-Chlorophenyl)-5-methylisoquinolineYield 60.5%

Reagents, catalysts & solvents 1

HCID 8404TetralinSolvent

Procedure

A mixture of 30 g of 1-(4-chlorophenyl)-5-methyl-3,4-dihydroisoquinoline and 30 g of diphenyl disulfide was dissolved in 800 ml of tetralin, and the solution was heated. After the reaction, the tetralin was distilled off under reduced pressure. The residue was dissolved in benzene, and extracted with a 2 N aqueous solution of hydrochloric acid. The aqueous layer was neutralized with an aqueous solution of sodium hydroxide, extracted with ether, and dried, followed by distilling off the solvent. Recrystallization of the residue from benzenecyclohexane afforded 18 g of 1-(4-chlorophenyl)-5-methylisoquinoline as colorless needles having a melting point of 122° to 123.5° C.

Workup

  1. temperaturethe solution was heated
  2. customAfter the reaction
  3. distillationthe tetralin was distilled off under reduced pressure
  4. dissolutionThe residue was dissolved in benzene
  5. extractionextracted with a 2 N aqueous solution of hydrochloric acid
  6. extractionextracted with ether
  7. customdried
  8. distillationby distilling off the solvent
  9. customRecrystallization of the residue from benzenecyclohexane

Sources & evidence

ORD record
ord-4f6af3b8064c41a3af263cf37f67db93
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

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