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

HRID 1157547Notes

Reaction equation

HRID 1157547 reaction equation
[CH3:1][N:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([N+:12]([O-])=O)=[CH:7][CH:8]=2)[CH2:3]1>CCOC(C)=O.[Pd]>[CH3:1][N:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([NH2:12])=[CH:7][CH:8]=2)[CH2:3]1

Participants

4

Reactant 1

HCID 221158282-Methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 129995062-Methyl-1,2,3,4-tetrahydroisoquinolin-7-amineYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-Methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline (3.0 g, 15.6 mmol) was dissolved in EtOAc (10 mL) and stirred vigorously with 10% Pd/C (0.3 g) under a hydrogen atmosphere at 55 PSI. The reaction was stirred for 15 h at rt. The reaction was filtered through celite and concentrated to provide 2.2 g (87%) of the desired 2-methyl-1,2,3,4-tetrahydro-7-isoquinolinamine product as a white powder. 1H NMR (400 MHz, DMSO-d6) δ 6.83 (d, J=8.3 Hz, 1H), 6.44 (d, J=8.0 Hz, 1H), 6.24 (s, 1H), 4.97 (s, 2H), 3.87 (m, 2H), 3.11 (t, J=6.4 Hz, 2H), 2.85-2.68 (m, 2H), 2.58 (s, 3H).

Workup

  1. filtrationThe reaction was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-f60a17eeb5564b8f8855d4a7b6b801f5
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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