{2-[6-(ethyloxy)-7-nitro-3,4-dihydro-1(2H)-quinolinyl]-2-oxoethyl}dimethylamine → 1-[(Dimethylamino)acetyl]-6-(ethyloxy)-1,2,3,4-tetrahydro-7-quinolinamine
Reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[N+:14]([O-])=O)[N:10]([C:17](=[O:22])[CH2:18][N:19]([CH3:21])[CH3:20])[CH2:9][CH2:8][CH2:7]2)[CH3:2].[H][H]>CO.[Pd]>[CH3:21][N:19]([CH2:18][C:17]([N:10]1[C:11]2[C:6](=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[C:13]([NH2:14])[CH:12]=2)[CH2:7][CH2:8][CH2:9]1)=[O:22])[CH3:20]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of {2-[6-(ethyloxy)-7-nitro-3,4-dihydro-1(2H)-quinolinyl]-2-oxoethyl}dimethylamine (5.8 g, 18.87 mmol) in degassed methanol (50.0 mL) was added to a suspension of 10% Pd/C (3.0 g, 16.36 mmol) in degassed methanol (5 mL) and maintained under a 50 psi hydrogen gas with rapid stirring for 16 hours. The suspension was purged with nitrogen, filtered through celite, all volatiles removed, and the resulting residue was purified by flash column chromatography to afford 1-[(dimethylamino)acetyl]-6-(ethyloxy)-1,2,3,4-tetrahydro-7-quinolinamine (2.85 g, 63%) as a viscous yellow liquid which solidified upon standing for 10 hours. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.80 (s, 1 H), 6.55 (s, 1 H), 4.52 (s, 2 H), 3.95 (q, J=6.89 Hz, 2 H), 3.61 (t, J=6.02 Hz, 2 H), 3.15 (s, 2 H), 2.55 (t, J=6.52 Hz 2 H), 2.20 (s, 6 H), 1.73-1.86 (m, 2 H), 1.32 (t, J=7.02 Hz, 3 H).
Workup
- customThe suspension was purged with nitrogen
- filtrationfiltered through celite
- customall volatiles removed
- customthe resulting residue was purified by flash column chromatography
Sources & evidence
- ORD record
- ord-1f8ccc2bb1cd489f846a82fb50f6d8b5
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07981903B2
Reaction notes
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