HCID 21436749, compound → 1,2,3,4-Tetrahydroisoquinolin-8-amine

HRID 2397921Notes

Reaction equation

HRID 2397921 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[CH:12]=[NH+:11][CH:10]=[CH:9]2)([O-])=O.[H][H]>[Pt]=O.CO>[NH2:1][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[CH2:12][NH:11][CH2:10][CH2:9]2

Participants

5

Reactant 2

HCID 21436749HCID 21436749, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 205232091,2,3,4-Tetrahydroisoquinolin-8-amine

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

The 2-lower alkyl-5,6,7, or 8-nitroisoquinolinium salt can be catalytically hydrogenated directly to a 2-lower alkyl-5,6,7 or 8-amino-1,2,3,4-tetrahydroisquinoline. The hydrogenation can be readily effected by use of a platinum oxide catalyst in methanol and a hydrogen pressure of about 25 to 100 psi. The hydrogenation proceeds at room temperature. After filtering to remove the catalyst, the filtrate can be worked up to obtain the 2-lower alkyl-5,6,7 or 8-amino-1,2,3,4-tetrahydroisoquinoline.

Workup

  1. customproceeds at room temperature
  2. filtrationAfter filtering
  3. customto remove the catalyst

Sources & evidence

ORD record
ord-778cb547fcb14cceaf5882ab74ffd555
Source dataset
uspto-grants-1977_05
Patent number
US04022900

Reaction notes

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