7-Amino-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one → HCID 21961482, compound

HRID 887618Notes

Reaction equation

HRID 887618 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:14])([CH3:13])[CH2:7][C:8](=O)[NH:9]2)=[CH:4][CH:3]=1>C1COCC1>[CH3:13][C:6]1([CH3:14])[C:5]2[C:10](=[CH:11][C:2]([NH2:1])=[CH:3][CH:4]=2)[NH:9][CH2:8][CH2:7]1

Participants

3

Reactant 1

HCID 144764787-Amino-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 21961482HCID 21961482, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture of 7-amino-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one (1.07 g, 5.62 mmol) and borane dimethylsulfide complex (1.60 ml, 16.9 mmol) in 40 ml of anhydrous THF was heated at reflux under N2 for 15 h. The solvents were removed under reduced pressure. The residue was heated at reflux in 20 ml of MeOH for 2 h, then 0.80 g of NaHCO3 was added, and the mixture was heated at reflux for 2 h. The mixture was filtered, condensed, and the residue was purified by flash column chromatography (5 to 10% of EtOAc in CH2Cl2). The titled compound was obtained as a viscous oil. MS (ES+): 176.9 (M+H)+. Calc'd for C11H16N—176.26.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under N2 for 15 h
  3. customThe solvents were removed under reduced pressure
  4. temperatureThe residue was heated
  5. temperatureat reflux in 20 ml of MeOH for 2 h
  6. addition0.80 g of NaHCO3 was added
  7. temperaturethe mixture was heated
  8. temperatureat reflux for 2 h
  9. filtrationThe mixture was filtered
  10. customcondensed
  11. customthe residue was purified by flash column chromatography (5 to 10% of EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-b61d5ff8e8b14edabf4aae5eb71ff89e
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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