7,8-Dichloroisoquinoline--hydrogen chloride (1/1) → Isoquinoline, 7,8-dichloro-1,2,3,4-tetrahydro-

HRID 461476Notes

Reaction equation

HRID 461476 reaction equation
Cl.[Cl:2][C:3]1[C:12]([Cl:13])=[C:11]2[C:6]([CH:7]=[CH:8][N:9]=[CH:10]2)=[CH:5][CH:4]=1>[Pt](=O)=O.CO>[Cl:2][C:3]1[C:12]([Cl:13])=[C:11]2[C:6]([CH2:7][CH2:8][NH:9][CH2:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 125950637,8-Dichloroisoquinoline--hydrogen chloride (1/1)

Product 1

HCID 123920Isoquinoline, 7,8-dichloro-1,2,3,4-tetrahydro-

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

The above prepared 7,8-dichloroisoquinoline hydrochloride was reduced in two portions by hydrogenation at 50-60 psi using 0.7 g. of platinum dioxide in 100 cc. of methanol, for one hour at ambient temperature. The mixture was filtered and concentrated. The residue was converted to the base using ammonium hydroxide and was extracted into ether. The extract was dried with magnesium sulfate, filtered and concentrated to give, as the residue, 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. extractionwas extracted into ether
  4. dry with materialThe extract was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-82d9fabeaf3d4c0083a05f890fb1ee67
Source dataset
uspto-grants-1977_12
Patent number
US04062961

Reaction notes

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