1-Methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride → 1-Methyl-1,2,3,4-tetrahydroisoquinolin-7-amine hydrochloride

HRID 369984Notes

Reaction equation

HRID 369984 reaction equation
[ClH:1].[CH3:2][CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N+:13]([O-])=O)[CH:11]=2)[CH2:6][CH2:5][NH:4]1.[H][H]>C(O)C.[Pd]>[ClH:1].[CH3:2][CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH2:13])[CH:11]=2)[CH2:6][CH2:5][NH:4]1

Participants

5

Reactant 2

HCID 215843101-Methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 215843601-Methyl-1,2,3,4-tetrahydroisoquinolin-7-amine hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1-methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride (2.0 g, 8.75 mmol) in ethanol (100 ml) and a catalytic quantity of 10% Pd-C was hydrogenated until no more hydrogen was taken up. The catalyst was filtered off, the solvent was concentrated to a small volume, ether was added and the precipitated solid was collected and dried: 1.39 g (78%), MS (M+H)+ 163.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe solvent was concentrated to a small volume, ether
  3. additionwas added
  4. customthe precipitated solid was collected
  5. customdried

Sources & evidence

ORD record
ord-1506bfd5213742bfa52baab91c29b1b0
Source dataset
uspto-grants-2000_10
Patent number
US06140322

Reaction notes

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