2-Bromoaniline → HCID 178471911、化合物

HRID 525876

反応式

HRID 525876 の反応式
[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].C(O[CH:12]=[C:13]([C:19](=[O:21])[CH3:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])C>C(O)(C)C>[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][CH:12]=[C:13]([C:19](=[O:21])[CH3:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15]

参加物

4

反応物 2

HCID 119922-BromoanilineHCID 97734Butanoic acid, 2-(ethoxymethylene)-3-oxo-, ethyl ester

生成物 1

HCID 178471911HCID 178471911、化合物収率 94.2%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

To a solution of 2-bromoaniline (2 g, 11.63 mmol) in Isopropanol (15 mL) stirred under nitrogen at room temperature was added neat ethyl 2-(ethoxymethylene)-3-oxobutanoate (2.165 g, 11.63 mmol) in one charge. The reaction mixture was stirred at room temperature for 20 min, at which time LCMS showed only a trace amount of product. The reaction mixture was heated to 75° C. and stirred for 20 min. LCMS showed complete conversion. The mixture was cooled to room temperature and concentrated under vacuum, during which time a large amount of material precipitated out. Filtration followed by a hexanes wash afforded ethyl 2-(((2-bromophenyl)amino)methylene)-3-oxobutanoate (3.8 g, 10.96 mmol, 94% yield) that was apx. 90% pure to be used in the next step. LCMS: (M+H)+: 312.0.

後処理

  1. additioncharge
  2. temperatureThe reaction mixture was heated to 75° C.
  3. stirringstirred for 20 min
  4. temperatureThe mixture was cooled to room temperature
  5. concentrationconcentrated under vacuum, during which time a large amount of material
  6. customprecipitated out
  7. filtrationFiltration
  8. washwash

出典と根拠

ORDレコード
ord-f8921492e0ae410692a0209eb6be74c0
出典データセット
uspto-grants-2016_05
特許番号
US09340556B2

関連ノート

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