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

HRID 887616Notes

Reaction equation

HRID 887616 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
120 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-65a19789063f4187bc8a123029223bf0
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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