2-(1-Methylethyl)-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline → 2-(1-Methylethyl)-6-(methyloxy)-1,2,3,4-tetrahydro-7-isoquinolinamine

HRID 1014370Notes

Reaction equation

HRID 1014370 reaction equation
[CH3:1][CH:2]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([N+:16]([O-])=O)=[C:9]([O:14][CH3:15])[CH:10]=2)[CH2:5]1)[CH3:3].[H][H]>C(OCC)(=O)C.[Pd].CO>[CH3:3][CH:2]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([NH2:16])=[C:9]([O:14][CH3:15])[CH:10]=2)[CH2:5]1)[CH3:1]

Participants

6

Reactant 2

HCID 594416842-(1-Methylethyl)-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 594419142-(1-Methylethyl)-6-(methyloxy)-1,2,3,4-tetrahydro-7-isoquinolinamineYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(1-methylethyl)-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline (0.24 g, 0.94 mmol) was dissolved in ethyl acetate (5 mL), treated with 10% palladium on carbon (50 mg, Aldrich), and then diluted with methanol (10 mL). The mixture was stirred under 60 psi of hydrogen pressure for 16 h in a Fischer-Porter apparatus. The pressure was released, the reaction vessel evacuated, and back-filled with nitrogen twice. The mixture was filtered through celite and the filtrate was concentrated to provide 2-(1-methylethyl)-6-(methyloxy)-1,2,3,4-tetrahydro-7-isoquinolinamine (206 mg, 0.94 mmol, 100%). 1H NMR (400 MHz, CDCl3) δ ppm 1.13 (d, J=6.6 Hz, 6 H), 2.71-2.81 (m, 4 H), 2.87 (tt, J=6.5, 6.5 Hz, 1 H), 3.59 (s, 2 H), 3.63 (bs, 2 H), 3.81 (s, 3 H), 6.40 (s, 1 H), 6.50 (s, 1 H).

Workup

  1. customthe reaction vessel evacuated
  2. additionback-filled with nitrogen twice
  3. filtrationThe mixture was filtered through celite
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f73ea873cfa347e6a82dda1fa5b27467
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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