N,N-dimethyl-3-[6-(methyloxy)-7-nitro-3,4-dihydro-1(2H)-quinolinyl]-3-oxo-1-propanamine → 1-[3-(Dimethylamino)propanoyl]-6-(methyloxy)-1,2,3,4-tetrahydro-7-quinolinamine
Reaction equation
[CH3:1][N:2]([CH3:22])[CH2:3][CH2:4][C:5]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([O:20][CH3:21])=[C:14]([N+:17]([O-])=O)[CH:15]=2)[CH2:10][CH2:9][CH2:8]1)=[O:6].[H][H]>CO.[Pd]>[CH3:22][N:2]([CH3:1])[CH2:3][CH2:4][C:5]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([O:20][CH3:21])=[C:14]([NH2:17])[CH:15]=2)[CH2:10][CH2:9][CH2:8]1)=[O:6]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
N,N-dimethyl-3-[6-(methyloxy)-7-nitro-3,4-dihydro-1(2H)-quinolinyl]-3-oxo-1-propanamine (crude from previous reaction, assumed 0.91 mmol) was dissolved in methanol (10 mL), treated with 10% palladium on carbon (50 mg, Aldrich), and 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 1-[3-(dimethylamino)propanoyl]-6-(methyloxy)-1,2,3,4-tetrahydro-7-quinolinamine (0.24 g, 93% over three steps). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.74-1.85 (m, 2 H), 2.09 (bs, 6 H), 2.51-2.60 (m, some signals may be underneath DMSO, 6 H), 3.58 (t, J=6.4 Hz, 2 H), 3.74 (s, 3 H), 4.60 (bs, 2 H), 6.60 (s, broadening due to amide rotomers, 2 H); ESIMS (M+H)+=278.
Workup
- customthe reaction vessel evacuated
- additionback-filled with nitrogen twice
- filtrationThe mixture was filtered through celite
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-3893f31864c248778ebb42b4beb4f39a
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07981903B2
Reaction notes
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