Dichloromethane → HCID 23336600, compound

HRID 903569Notes

Reaction equation

HRID 903569 reaction equation
[Cl:1][C:2]1[C:3]([SH:12])=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[N:9][CH:8]=[CH:7]2.C(Cl)Cl>CO>[ClH:1].[Cl:1][C:2]1[C:3]([SH:12])=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][NH:9][CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 20551392HCID 20551392, compound

Product 1

HCID 23336600HCID 23336600, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of (11.7 g., 0.06 m.) 8-chloro-7-mercaptoisoquinoline in 150 ml. of methylene chloride was added a solution of 1 M borane-methylsulfide complex (120 ml., 0.12 m.). The addition was carried out dropwise with stirring under a nitrogen atmosphere. After stirring for half an hour the reaction mixture was refluxed for 2.5 hours, cooled to 5° C., and treated with 135 ml. of methanol dropwise. The reaction mixture was evaporated to a residue under reduced pressure and was then repeatedly evaporated from methanol. The residue was dissolved in methanol and treated with ethereal hydrogen chloride. The resulting precipitate was collected by filtration and dried to give 8-chloro-7-mercapto-1,2,3,4-tetrahydroisoquinoline hydrochloride, m.p. 230°-234° C. dec.

Workup

  1. additionThe addition
  2. stirringAfter stirring for half an hour the reaction mixture
  3. temperaturewas refluxed for 2.5 hours
  4. additiontreated with 135 ml
  5. customThe reaction mixture was evaporated to a residue under reduced pressure
  6. customwas then repeatedly evaporated from methanol
  7. dissolutionThe residue was dissolved in methanol
  8. additiontreated with ethereal hydrogen chloride
  9. filtrationThe resulting precipitate was collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-d001546a510240c98be3d62879ba5466
Source dataset
uspto-grants-1980_10
Patent number
US04228170

Reaction notes

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