HCID 59441761, compound → HCID 59442100, compound

HRID 1014393Notes

Reaction equation

HRID 1014393 reaction equation
[CH3:1][N:2]([CH3:20])[CH2:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([CH3:19])=[C:13]([N+:16]([O-])=O)[CH:14]=2)[CH2:9][CH2:8][CH2:7]1)=[O:5]>CO.[Pd]>[CH3:20][N:2]([CH2:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([CH3:19])=[C:13]([NH2:16])[CH:14]=2)[CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:1]

Participants

4

Reactant 1

HCID 59441761HCID 59441761, compound

Product 1

HCID 59442100HCID 59442100, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

10% Pd on carbon (0.5 g, 17.37 mmol) was placed under N2 atm. MeOH (20 mL) was added, followed by a solution of N,N-dimethyl-2-(6-methyl-7-nitro-3,4-dihydro-1(2H)-quinolinyl)-2-oxoethanamine (2.07 g, 7.46 mmol) in MeOH (80 mL). The mixture was placed under H2 atm via balloon and maintained for 1 day. The resulting mixture was filtered through a pad of Celite using MeOH. The filtrate was concentrated, the residue was taken up into Et2O and concentrated again to afford 1-[(dimethylamino)acetyl]-6-methyl-1,2,3,4-tetrahydro-7-quinolinamine as a grey solid (1.55 g, 84%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.71-1.87 (m, 2H), 1.99 (s, 3H), 2.20 (s, 6H), 2.45-2.58 (m, 2H), 3.18 (s, 2H), 3.61 (t, J=6.13 Hz, 2H), 4.66 (br s, 2H), 6.69 (s, 1H), 6.78 (br s, 1H); ESIMS (M+H)+=248.17.

Workup

  1. temperaturemaintained for 1 day
  2. filtrationThe resulting mixture was filtered through a pad of Celite
  3. concentrationThe filtrate was concentrated
  4. concentrationconcentrated again

Sources & evidence

ORD record
ord-713d48f7dac74ab2868ad9bb40805ef7
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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