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

HRID 1288450Notes

Reaction equation

HRID 1288450 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-55b1cc5ba5f549b0aa0e37d1b161e5c3
Source dataset
uspto-grants-1976_10
Patent number
US03988339

Reaction notes

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