(3-Methoxy-5,6,7,8-tetrahydroquinolin-8-yl)-azide → (3-Methoxy-5,6,7,8-tetrahydroquinolin-8-yl)-amine

HRID 983623

Reaction equation

HRID 983623 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6]2[CH:7]([N:13]=[N+]=[N-])[CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1.[H][H]>[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6]2[CH:7]([NH2:13])[CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1

Participants

4

Reactant 2

HCID 22018805(3-Methoxy-5,6,7,8-tetrahydroquinolin-8-yl)-azideHCID 178418361HCID 178418361, compound

Product 1

HCID 22018774(3-Methoxy-5,6,7,8-tetrahydroquinolin-8-yl)-amineYield 98.2%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of (3-methoxy-5,6,7,8-tetrahydroquinolin-8-yl)-azide (0.33 g, 1.6 mmol) in MEOH (16 mL) was added palladium on activated carbon, (10%, 50 mg) and the reaction mixture stirred under 1 atmosphere of hydrogen for 4 h. The mixture was filtered through celite, the cake washed with methanol and the solvent from the eluent removed in vacuo to give crude (3-methoxy-5,6,7,8-tetrahydroquinolin-8-yl)-amine as a yellow oil (0.28 g, 96%). 1H NMR (CDCl3) δ1.75 (m, 2H), 1.97 (m, 1H), 2.17 (m, 1H), 2.77 (m, 2H), 3.81 (s, 3H), 3.98 (t, 1H, J=4.5 Hz), 6.88 (d, 1H, J=1.5 Hz), 8.12 (d, 1H, J=1.5 Hz).

Workup

  1. filtrationThe mixture was filtered through celite
  2. washthe cake washed with methanol
  3. customthe solvent from the eluent removed in vacuo

Sources & evidence

ORD record
ord-2f46ff4ae9024556a07d82f8e2d534ff
Source dataset
uspto-grants-2005_03
Patent number
US06864265B2

Linked notes

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