Methanol → HCID 59441954, compound

HRID 1014382Notes

Reaction equation

HRID 1014382 reaction equation
[CH3:1][C:2]1([CH3:23])[C:11]2[C:6](=[CH:7][C:8]([N+:14]([O-])=O)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]([C:17](=[O:22])[CH2:18][N:19]([CH3:21])[CH3:20])[CH2:4][CH2:3]1.CO.[H][H]>C(OCC)(=O)C.O.[Pd]>[CH3:21][N:19]([CH2:18][C:17]([N:5]1[C:6]2[C:11](=[CH:10][C:9]([O:12][CH3:13])=[C:8]([NH2:14])[CH:7]=2)[C:2]([CH3:23])([CH3:1])[CH2:3][CH2:4]1)=[O:22])[CH3:20]

Participants

7

Reactant 3

HCID 887MethanolHCID 59441838HCID 59441838, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59441954HCID 59441954, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

{2-[4,4-dimethyl-6-(methyloxy)-7-nitro-3,4-dihydro-1(2H)-quinolinyl]-2-oxoethyl}dimethylamine (assumed 2.8 mmol) was dissolved in a mixture of ethyl acetate (50 mL) and water (5 mL) and transferred to a Fischer Porter apparatus. 10% Palladium on carbon (500 mg, Aldrich) was added followed by methanol (5 mL) and the mixture stirred under 60 psi hydrogen pressure for 2 h. 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-[(dimethylamino)acetyl]-4,4-dimethyl-6-(methyloxy)-1,2,3,4-tetrahydro-7-quinolinamine (724 mg, 2.49 mmol, 89% over three steps). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.20 (s, 6 H), 1.62-1.68 (m, 2 H), 2.20 (s, 6 H), 3.17 (s, 2 H), 3.62-3.69 (m, 2 H), 3.75 (s, 3 H), 4.58 (bs, 2 H), 6.56-6.94 (s at 6.71 on top of a very broad singlet caused by amide rotomers, 2 H); ESIMS (M+H)+=292.

Workup

  1. customthe reaction vessel evacuated
  2. additionback-filled with nitrogen twice
  3. filtrationThe mixture was filtered through celite
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1d404fbf8b1e41fd814858daf6c5e6ea
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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