1,2,3,4-Tetrahydro-7-nitroisoquinoline → 1,2,3,4-Tetrahydroisoquinolin-7-amine

HRID 1640214Notes

Reaction equation

HRID 1640214 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][NH:10][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[CH2:11]1[C:12]2[C:7](=[CH:6][CH:5]=[C:4]([NH2:1])[CH:13]=2)[CH2:8][CH2:9][NH:10]1

Participants

4

Reactant 1

HCID 64248331,2,3,4-Tetrahydro-7-nitroisoquinoline

Product 1

HCID 115863231,2,3,4-Tetrahydroisoquinolin-7-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 7-nitro-1,2,3,4-tetrahydro-isoquinoline (38 g, 0.21 mol) and 10% Pd/C (5 g) in MeOH (400 mL) was stirred under an atmosphere of hydrogen at rt for 16 h and then filtered through Celite. Removal of solvent gave 1,2,3,4-tetrahydroisoquinolin-7-amine as a pink solid in quantitative yield. MS: 149.

Workup

  1. filtrationfiltered through Celite
  2. customRemoval of solvent

Sources & evidence

ORD record
ord-908d3b995d1749618ffefec1817c38c9
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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