1-(3,4-Dihydro-6-methoxy-7-nitro-1(2H)-quinolinyl)ethanone → HCID 59442131, compound

HRID 1014374Notes

Reaction equation

HRID 1014374 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([O:17][CH3:18])=[C:11]([N+:14]([O-])=O)[CH:12]=2)[CH2:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([O:17][CH3:18])=[C:11]([NH2:14])[CH:12]=2)[CH2:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 594421241-(3,4-Dihydro-6-methoxy-7-nitro-1(2H)-quinolinyl)ethanone

Product 1

HCID 59442131HCID 59442131, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-acetyl-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroquinoline (350 mg, 1.40 mmol) in ethyl acetate (20 mL) was taken in a Fischer Porter apparatus and treated with 10% palladium on carbon (100 mg, Aldrich). After rinsing the sides of the flask with ethyl acetate, methanol (30 mL) was added and the mixture was stirred under 60 psi hydrogen pressure for 16 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-acetyl-6-(methyloxy)-1,2,3,4-tetrahydro-7-quinolinamine (270 mg, 1.23 mmol, 88%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.74-1.86 (m, 2 H), 2.06-2.13 (m, 3 H), 2.53-2.61 (m, 2 H), 3.56-3.61 (m, 2 H), 3.73 (s, 3 H), 4.55 (bs, 2 H), 6.46-6.91 (m, broadened signals caused by amide rotomers, 2 H).

Workup

  1. washAfter rinsing the sides of the flask with ethyl acetate, methanol (30 mL)
  2. additionwas added
  3. customthe reaction vessel evacuated
  4. additionback-filled with nitrogen twice
  5. filtrationThe mixture was filtered through celite
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-44cbd215e89549a2888c12a7a59883e9
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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