Water → 6-Bromo-1,4,4-trimethyl-3,4-dihydroquinolin-2(1H)-one

HRID 51705

Reaction equation

HRID 51705 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:15])[C:9](=[O:14])[CH:10]=[C:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].O>CCCCCC.ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[N:8]([CH3:15])[C:9](=[O:14])[CH2:10][C:11]2([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 22568913N-(4-Bromophenyl)-N-methyl-3-methyl-2-butenamide2×

Product 1

HCID 225690036-Bromo-1,4,4-trimethyl-3,4-dihydroquinolin-2(1H)-oneYield 26.4%

Reagents, catalysts & solvents 1

HCID 21226440Methylenechloride HexaneSolvent

Procedure

N-(4-bromophenyl)-N-methyl-3-methyl-2-butenamide (Intermediate 54, 6.42 g, 24 mmol) was heated to 130° C. and aluminum chloride (5 g, 37.4 mmol) was added in portions over 0.5 h. The reaction mixture was stirred for 1 hour at the same temperature and then cooled to room temperature. Ice was added cautiously to the solid, followed by ˜200 mL of iced water. The reaction mixture was then extracted with ether (×2) and dichloromethane (×1) and the combined organic phase was dried over anhydrous magnesium sulfate and evaporated in vacuo to yield a brown solid. The solid was treated with hexane-dichloromethane and filtered to afford 1.7 g of product. The mother liquor was evaporated and purified by flash column chromatography on silica gel (230-400 mesh) to afford 2.9 g of the title compound as a solid (total 72%).

Workup

  1. additionIce was added cautiously to the solid
  2. extractionThe reaction mixture was then extracted with ether (×2) and dichloromethane (×1)
  3. dry with materialthe combined organic phase was dried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customto yield a brown solid
  6. filtrationfiltered

Sources & evidence

ORD record
ord-5a5f813706344ec4a1f9df87fe3c3e8a
Source dataset
uspto-grants-2004_03
Patent number
US06713647B2

Linked notes

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