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

HRID 24136

反応式

HRID 24136 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21226440Methylenechloride Hexane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-b85b6f9e5d254a01ae011c966d72a4e5
出典データセット
uspto-grants-2005_02
特許番号
US06855512B2

関連ノート

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