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

HRID 887616노트

반응식

HRID 887616 반응식
[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

참가 물질

4

반응물 2

HCID 6451240Aluminum(III) ChlorideHCID 86630779HCID 86630779, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 7964Chlorobenzene용매

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온도
120 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-65a19789063f4187bc8a123029223bf0
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247430B2

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