2-Butenamide, N-(4-bromophenyl)-3-methyl- → 6-bromo-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one

HRID 1840871Notes

Reaction equation

HRID 1840871 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:18])[CH:14]=[C:15]([CH3:17])[CH3:16])=[CH:8][CH:7]=1>>[Br:5][C:6]1[CH:7]=[C:8]2[C:9](=[CH:10][CH:11]=1)[NH:12][C:13](=[O:18])[CH2:14][C:15]2([CH3:16])[CH3:17]

Participants

3

Reactant 2

HCID 5320952-Butenamide, N-(4-bromophenyl)-3-methyl-2×HCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 107295896-bromo-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-oneYield 68.2%

Conditions

Temperature
80 °C

Procedure

Aluminum chloride (5 g, 37.5 mmol) was added portionwise into N-(4-bromophenyl)-3-methylbut-2-enoic amide (Intermediate 3, 7.69 g, 30.0 mmol) in a 500 mL beaker at 130° C. over 1 h. The beaker was then cooled to 80° C. and another portion of aluminum chloride (1 g, 7.5 mmol) was added. After stirring at 80° C. for 0.5 h, the beaker was cooled with an ice-bath and ice was added slowly into the mixture. The resulting slurry was then extracted with ether (3×10 mL). The combined organic layer was washed with brine (1×10 mL), saturated NaHCO3 (1×10 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chomatography (75:25 hexane/ethyl acetate) yielded the title compound as a pale yellow solid (5.20 g, 68% yield).

Workup

  1. temperaturethe beaker was cooled with an ice-bath
  2. additionice was added slowly into the mixture
  3. extractionThe resulting slurry was then extracted with ether (3×10 mL)
  4. washThe combined organic layer was washed with brine (1×10 mL), saturated NaHCO3 (1×10 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated at reduced pressure
  7. customPurification by flash chomatography (75:25 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-70ce6fe112794e36b1a9944c2327f367
Source dataset
uspto-grants-2004_01
Patent number
US06683092B1

Reaction notes

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