HCID 21436737, compound → HCID 21436740, compound

HRID 2397925Notes

Reaction equation

HRID 2397925 reaction equation
[Br-:1].[N+:2]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][N+:9]([CH2:15][CH2:16][CH3:17])=[CH:10]2)([O-])=O>CO.[Pt]=O>[BrH:1].[NH2:2][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][N:9]([CH2:15][CH2:16][CH3:17])[CH2:10]2

Participants

4

Reactant 1

HCID 21436737HCID 21436737, compound

Product 1

HCID 21436740HCID 21436740, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

5-Nitro-2-n-propylisoquinolinium bromide (8.2 g) was dissolved in methanol (150 ml) and the solution hydrogenated over platinum oxide (0.6 g) at 45 psi. When the hydrogenation was complete, the catalyst was removed by filtration and the solvent removed in vacuo to leave a light orange solid residue of 5-amino-2-n-propyl-1,2,3,4-tetrahydroisoquinoline hydrobromide (7.5 g). This residue was recrystallized from ethanol and the product obtained as pale orange crystals, m.p. 238°-239.5° C.

Workup

  1. customthe catalyst was removed by filtration
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-cceff6d68eeb4094a9558e8d4d59a204
Source dataset
uspto-grants-1977_05
Patent number
US04022900

Reaction notes

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