Aluminum(III) Chloride → N-(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)acetamide

HRID 887616ノート

反応式

HRID 887616 の反応式
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([NH:11][C:12](=[O:17])[CH:13]=[C:14]([CH3:16])[CH3:15])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].CC1(C)C2C(=CC([N+]([O-])=O)=CC=2)NC1.[Al+3].[Cl-].[Cl-].[Cl-]>ClC1C=CC=CC=1>[CH3:15][C:14]1([CH3:16])[C:8]2[C:7](=[CH:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:10][CH:9]=2)[NH:11][C:12](=[O:17])[CH2:13]1

参加物

4

反応物 2

HCID 6451240Aluminum(III) ChlorideHCID 86630779HCID 86630779、化合物

生成物 1

HCID 14476477N-(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)acetamide

試薬・触媒・溶媒 1

HCID 7964Chlorobenzene溶媒

反応条件

温度
120 °C

実験手順

The mixture of 3,3-dimethyl-6-nitroindoline 3-Methyl-but-2-enoic acid (3-acetylamino-phenyl)-amide (1.05 g, 4.52 mmol) and AlCl3 (5.0 g, 37.5 mmol, Aldrich, 99.99%) in 50 ml of anhydrous chlorobenzene was stirred at 120° C. (oil bath temperature) under N2 overnight, cooled to RT, poured into 10 ml of ice cold HCl, stirred for 30 min, and extracted with EtOAc. The organic portions were combined, washed with brine, dried with Na2SO4, filtered, condensed, and purified by flash column chromatography (1% of MeOH in CH2Cl2). The titled compound was obtained as an off-white solid. MS (ES+): 233.2 (M+H)+. Calc'd for C13H16N2O2—232.28.

後処理

  1. temperaturecooled to RT
  2. stirringstirred for 30 min
  3. extractionextracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. customcondensed
  8. custompurified by flash column chromatography (1% of MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-65a19789063f4187bc8a123029223bf0
出典データセット
uspto-grants-2012_08
特許番号
US08247430B2

反応ノート

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