HCID 24973453, compound → 5-Amino-1-methyl-2(1H)-quinolinone

HRID 2404380Notes

Reaction equation

HRID 2404380 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-])=O)[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]1=[O:15].[H][H]>O1CCCC1.[Pd]>[NH2:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[CH:5]=[CH:4][C:3](=[O:15])[N:2]2[CH3:1]

Participants

5

Reactant 2

HCID 24973453HCID 24973453, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 672672595-Amino-1-methyl-2(1H)-quinolinoneYield 75.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 50A (2.16 g, 10.6 mmol) in tetrahydrofuran (50 mL) was added to 5% Pd—C, wet (0.432 g, 4.06 mmol) in a 250 mL stainless steel pressure bottle. After 3 hours at about room temperature under 30 psi of hydrogen pressure, the mixture was filtered through a nylon membrane and concentrated. EtOH (22 mL) was added, and the yellow slurry was sonicated for 5 minutes and filtered, washing with EtOH (10 mL). The yellow solid was dried in a vacuum oven at 50° C. to provide the title compound (1.40 g, 8.04 mmol, 75% yield). MS (DCI) m/z 175 (M+N)+.

Workup

  1. filtrationthe mixture was filtered through a nylon membrane
  2. concentrationconcentrated
  3. additionEtOH (22 mL) was added
  4. customthe yellow slurry was sonicated for 5 minutes
  5. filtrationfiltered
  6. washwashing with EtOH (10 mL)
  7. customThe yellow solid was dried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-6b76ce1f9f69432fa1fed81ec47d7915
Source dataset
uspto-grants-2014_08
Patent number
US08802711B2

Reaction notes

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