HCID 59441783, compound → HCID 59441854, compound

HRID 1014305Notes

Reaction equation

HRID 1014305 reaction equation
[CH3:1][N:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([N+:14]([O-])=O)=[C:7]([O:12][CH3:13])[CH:8]=2)[CH2:3]1>CO.[OH-].[OH-].[Pd+2]>[CH3:1][N:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([NH2:14])=[C:7]([O:12][CH3:13])[CH:8]=2)[CH2:3]1

Participants

4

Reactant 1

HCID 59441783HCID 59441783, compound

Product 1

HCID 59441854HCID 59441854, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-methyl-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline and Pd(OH)2(1 g) in MeOH(100 mL) was stirred under H2 at room temperature for 5 h. The solution was filtered and all solvents were removed under reduced pressure to give 2-methyl-6-(methyloxy)-1,2,3,4-tetrahydro-7-isoquinolinamine (2 g, 77.2%). 1H NMR (400 MHz, CDCl3) δ ppm 6.51 (s, 1 H), 6.38 (s, 1 H), 3.81 (s, 3 H), 3.64 (s, 2 H), 3.43 (s, 2 H), 2.81 (t, J=5.77 Hz, 2 H), 2.64 (t, J=5.90 Hz, 2 H), 2.42 (s, 3H).

Workup

  1. filtrationThe solution was filtered
  2. customall solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-2847210ffe9547bea8849aa0aa1cae3d
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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