Aluminum(III) Chloride → 7-Bromo-4,4,6-trimethyl-3,4-dihydro-1H-quinoline-2-one

HRID 1790196

反応式

HRID 1790196 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:15])[CH:11]=[C:12]([CH3:14])[CH3:13])[CH:5]=[CH:6][C:7]=1[CH3:8].[Cl-].[Al+3].[Cl-].[Cl-]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([C:12]([CH3:13])([CH3:14])[CH2:11][C:10](=[O:15])[NH:9]2)=[CH:6][C:7]=1[CH3:8]

参加物

3

反応物 2

HCID 6451240Aluminum(III) ChlorideHCID 60729710N-(3-Bromo-4-methylphenyl)-3-methyl-2-butenamide

生成物 1

HCID 219664237-Bromo-4,4,6-trimethyl-3,4-dihydro-1H-quinoline-2-one収率 65.7%

実験手順

To a solution of 3-methyl-but-2-enoic acid (3-bromo-4-methyl-phenyl)-amide (70.0 g, 261 mmol) at 90° C. was added portion wise, under argon, with vigorous stirring aluminum chloride (52.3 g, 391 mmol) over 1.5 hr. The reaction mixture was stirred for 2 hours at 110–120° C. The reaction mixture was cooled to room temperature and ice-water was carefully added. The solution was extracted with dichloromethane and the organic washed with 2N HCl, water, saturated aqueous NaHCO3, water and brine, dried (Mg2SO4), filtered and evaporated. The residue was crystallized from dichloromethane/hexane to give 46 g of 7-bromo-4,4,6-trimethyl-3,4-dihydro-1H-quinoline-2-one. The mother liquor was further chromatographed on silica gel (20% ethyl acetate in hexane) to give 6.2 g more of product. (75%). 1H NMR (300 MHz; CDCl3): 1.30 (s, 6 H), 2.33 (s, 3 H), 2.46 (s, 2 H), 7.07 (s, 1 H), 7.10 (s, 1 H), 9.87 (br s, 1 H).

後処理

  1. extractionThe solution was extracted with dichloromethane
  2. washthe organic washed with 2N HCl, water, saturated aqueous NaHCO3, water and brine
  3. dry with materialdried (Mg2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallized from dichloromethane/hexane

出典と根拠

ORDレコード
ord-dbf0f186371046a78ad1fca5bc79a0a1
出典データセット
uspto-grants-2006_07
特許番号
US07071218B2

関連ノート

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