N-ethyl-N-methyl-2-[6-(methyloxy)-7-nitro-3,4-dihydro-1(2H)-quinolinyl]-2-oxoethanamine → 1-{[Ethyl(methyl)amino]acetyl}-6-(methyloxy)-1,2,3,4-tetrahydro-7-quinolinamine

HRID 1014295Notes

Reaction equation

HRID 1014295 reaction equation
[CH2:1]([N:3]([CH3:22])[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])[CH3:2]>[Pd].CO>[CH2:1]([N: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])[CH3:22])[CH3:2]

Participants

4

Reactant 1

HCID 59441978N-ethyl-N-methyl-2-[6-(methyloxy)-7-nitro-3,4-dihydro-1(2H)-quinolinyl]-2-oxoethanamine

Product 1

HCID 673169641-{[Ethyl(methyl)amino]acetyl}-6-(methyloxy)-1,2,3,4-tetrahydro-7-quinolinamineYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N-ethyl-N-methyl-2-[6-(methyloxy)-7-nitro-3,4-dihydro-1(2 H)-quinolinyl]-2-oxoethanamine (2.02 g, 6.57 mmol) and 10% palladium on carbon (1.05 g) in methanol (55 mL) was maintained under 40 psi of H2 gas in a pressure flask for 24 hours. The solution was purged with nitrogen, filtered through celite, taken to a residue under reduced pressure, and purified by column chromatography to afford 1-{[ethyl(methyl)amino]acetyl}-6-(methyloxy)-1,2,3,4-tetrahydro-7-quinolinamine (1.16 g, 64% yield) as a dark orange oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.82 (s, 1H), 6.56 (s, 1 H), 4.54 (s, 2 H), 3.72 (s, 3 H), 3.61 (t, J=5.82 Hz, 2 H), 3.25 (s, 2 H), 2.57 (t, J=6.22 Hz, 2 H), 2.43 (q, J=7.02 Hz, 2 H), 2.20 (s, 3 H), 1.70-1.89 (m, 2 H), 0.84-1.03 (m, 3 H).

Workup

  1. customThe solution was purged with nitrogen
  2. filtrationfiltered through celite
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-c3729fe0520947baab4e4958becfa158
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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