HCID 59441699, compound → HCID 59442022, compound

HRID 1014366Notes

Reaction equation

HRID 1014366 reaction equation
[CH3:1][N:2]([CH3:21])[CH2:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:19][CH3:20])=[C:13]([N+:16]([O-])=O)[CH:14]=2)[CH2:9][CH2:8][CH2:7]1)=[O:5].[H][H]>CO.[Pd]>[CH3:21][N:2]([CH2:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:19][CH3:20])=[C:13]([NH2:16])[CH:14]=2)[CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:1]

Participants

5

Reactant 2

HCID 59441699HCID 59441699, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59442022HCID 59442022, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N,N-dimethyl-2-[6-(methyloxy)-7-nitro-3,4-dihydro-1(2H)-quinolinyl]-2-oxoethanamine (crude from previous reaction, assumed 0.91 mmol) was dissolved in methanol (5 mL), treated with 10% palladium on carbon (40 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, the filtrate was concentrated and purified by chromatography on SiO2 (0 to 20% methanol/dichloromethane) to provide 1-[(dimethylamino)acetyl]-6-(methyloxy)-1,2,3,4-tetrahydro-7-quinolinamine (0.18 g, 0.68 mmol, 75% over three steps). 1H NMR (400 MHz, CDCl3) δ ppm 1.88-1.97 (m, J=6.5, 6.5, 6.5, 6.5 Hz, 2 H), 2.35 (s, 6 H), 2.65 (m, 2 H), 3.24 (s, 2 H), 3.74-3.80 (m, 2 H), 3.84 (s, 3 H), 6.55 (s, 1 H), 6.76 (very broad singlet due to amide rotomers, 1 H), aniline NH2 not visible probably due to fast exchange.

Workup

  1. customthe reaction vessel evacuated
  2. additionback-filled with nitrogen twice
  3. filtrationThe mixture was filtered through celite
  4. concentrationthe filtrate was concentrated
  5. custompurified by chromatography on SiO2 (0 to 20% methanol/dichloromethane)

Sources & evidence

ORD record
ord-9587e9ef506843a195dc7df64e5abdec
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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