Acetic Anhydride → 6-(4-Chloro-benzoyl)-4-(3-iodo-phenyl)-1H-quinolin-2-one

HRID 2298980Notes

Reaction equation

HRID 2298980 reaction equation
[NH2:1][CH:2]1[CH:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([I:16])[CH:11]=2)=O)[CH:6]=[C:5]([C:17](=[O:25])[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH:4]=[CH:3]1.C(N(CC)CC)C.[C:33](OC(=O)C)(=[O:35])[CH3:34]>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([C:17]([C:5]2[CH:6]=[C:7]3[C:2](=[CH:3][CH:4]=2)[NH:1][C:33](=[O:35])[CH:34]=[C:8]3[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([I:16])[CH:11]=2)=[O:25])=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 15489628[6-Amino-3-(4-chloro-benzoyl)-cyclohexa-2,4-dienyl]-(3-iodo-phenyl)-methanone

Product 1

HCID 154896296-(4-Chloro-benzoyl)-4-(3-iodo-phenyl)-1H-quinolin-2-one

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

[6-Amino-3-(4-chloro-benzoyl)-cyclohexa-2,4-dienyl]-(3-iodo-phenyl)-methan-one (60 g, 130 mMol) was dissolved in anhydrous toluene (450 mL) under an atmosphere of dry N2. To this solution was added 180 mL of triethylamine (NEt3), 50 mL of acetic anhydride (Ac2O) and 1.60 g (13.0 mMol) of 4-dimethylaminopyridine (DMAP). The reaction mixture was then heated to reflux and stirred at this temperature for 20 hours. The reaction mixture was cooled to ambient temperature and the precipitate was collected via suction filtration. The solid was washed with ethyl ether (Et2O) and dried under vacuum to give of the titled compound (63 g) which was used without further purification.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux
  3. filtrationthe precipitate was collected via suction filtration
  4. washThe solid was washed with ethyl ether (Et2O)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-be9b192ef10f408793ae4c57ab254bd9
Source dataset
uspto-grants-2002_12
Patent number
US06495564B1

Reaction notes

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