Methanol → HCID 59441929, compound

HRID 1014383Notes

Reaction equation

HRID 1014383 reaction equation
[CH3:1][C:2]1([CH3:18])[C:11]2[C:6](=[CH:7][C:8]([N+:14]([O-])=O)=[C:9]([O:12][CH3:13])[CH:10]=2)[NH:5][C:4](=[O:17])[CH2:3]1.CO.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:14][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([CH3:1])([CH3:18])[CH2:3][C:4](=[O:17])[NH:5]2)=[CH:10][C:9]=1[O:12][CH3:13]

Participants

6

Reactant 3

HCID 887MethanolHCID 59441860HCID 59441860, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59441929HCID 59441929, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4,4-dimethyl-6-(methyloxy)-7-nitro-3,4-dihydro-2(1H)-quinolinone (250 mg, 1.00 mmol) was dissolved in ethyl acetate (10 mL) and transferred to a Fischer Porter apparatus. 10% Palladium on carbon (250 mg, Aldrich) was added followed by methanol (20 mL) and the mixture 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 7-amino-4,4-dimethyl-6-(methyloxy)-3,4-dihydro-2(1H)-quinolinone (213 mg, 0.92 mmol, 92%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.16 (s, 6 H), 2.22 (s, 2 H), 3.72 (s, 3 H), 4.66 (s, 2 H), 6.20 (s, 1 H), 6.67 (s, 1 H), 9.76 (s, 1 H).

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-53b632e517b447df96f0e63ee3e31e5d
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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