HCID 532094, compound → 3,4-Dihydro-6-methoxy-4,4-dimethyl-2(1H)-quinolinone

HRID 1014378Notes

Reaction equation

HRID 1014378 reaction equation
[CH3:1][C:2]([CH3:15])=[CH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:5].[Cl-].[Cl-].[Cl-].[Al+3]>ClCCl>[CH3:1][C:2]1([CH3:15])[C:8]2[C:7](=[CH:12][CH:11]=[C:10]([O:13][CH3:14])[CH:9]=2)[NH:6][C:4](=[O:5])[CH2:3]1

Participants

4

Reactant 2

HCID 532094HCID 532094, compoundHCID 6451240Aluminum(III) Chloride

Product 1

HCID 594418093,4-Dihydro-6-methoxy-4,4-dimethyl-2(1H)-quinolinoneYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-methyl-N-[4-(methyloxy)phenyl]-2-butenamide (5.8 g, 28 mmol) in dichloromethane (250 mL) was treated with aluminum trichloride (13 g, 97 mmol, Aldrich). The mixture was refluxed for 7 h, cooled, and then poured over ice. The organic layer was separated, dried over magnesium sulfate, filtered, and concentrated to give 4,4-dimethyl-6-(methyloxy)-3,4-dihydro-2(1H)-quinolinone (4.5 g, 77%). 1H NMR (400 MHz, DMSO-d6) δppm 1.20 (s, 6 H), 2.29 (s, 2 H), 3.71 (s, 3 H), 6.72-6.81 (m, 2 H), 6.83 (d, J=2.6 Hz, 1 H), 9.97 (s, 1 H).

Workup

  1. temperatureThe mixture was refluxed for 7 h
  2. temperaturecooled
  3. additionpoured over ice
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-838a1785a9074a4fab6b22f1d4c67c68
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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