Potassium Carbonate → N-[4-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)phenyl]benzamide

HRID 1603087Notes

Reaction equation

HRID 1603087 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[C:17]([NH:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O.O>[C:17]([NH:25][C:26]1[CH:27]=[CH:28][C:29]([C:30]([N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][CH2:2]2)=[O:31])=[CH:33][CH:34]=1)(=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 694601,2,3,4-TetrahydroquinolineHCID 125009584-Benzoylaminobenzoyl chloride

Product 1

HCID 10642000N-[4-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)phenyl]benzamideYield 74.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a solution of 1,2,3,4-tetrahydroquinoline (28.7 g) in acetone (400 ml) and water (200 ml) is added potassium carbonate (38.8 g) and further thereto is added 4-benzoylaminobenzoyl chloride (56 g) under ice-cooling. The mixture is stirred at room temperature overnight. Water is added to the reaction mixture, and the mixture is extracted with dichloromethane. The extract is dried over magnesium sulfate, and the solvent is distilled off under reduced pressure. The resulting residue is purified by silica gel column chromatography and recrystallized from methanol to give 1-[4-(benzoylamino)benzoyl-]-1,2,3,4-tetrahydroquinoline (57 g) as white powder, m.p. 202.5-203.5° C.

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with dichloromethane
  3. dry with materialThe extract is dried over magnesium sulfate
  4. distillationthe solvent is distilled off under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-5416b3f320964db99496e17142cb5cd2
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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