Water → HCID 19030932, compound

HRID 266827Notes

Reaction equation

HRID 266827 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.C(N(CC)CC)C.[N:17]1([C:28]2[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=2)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH2:20][C:18]1=[O:19].O>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:32]([C:31]2[CH:30]=[CH:29][C:28]([N:17]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21][CH2:20][C:18]3=[O:19])=[CH:36][CH:35]=2)=[O:33])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7732P-AnisidineHCID 8471TriethylamineHCID 53659360HCID 53659360, compound

Product 1

HCID 19030932HCID 19030932, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of p-anisidine (0.11 g) in chloroform (5 ml) is added triethylamine (0.15 g) and thereto is added with stirring a solution of 4-(3,4-dihydrocarbostyril-1-yl)benzoic acid chloride obtained above in chloroform (2 ml) 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, washed with water and dried with magnesium sulfate. The solvent is distilled off under reduced pressure and the resulting residue is crystallized from diethyl ether and further recrystallized from ethanol/diethyl ether/n-hexane to give 1-[4-(4-methoxyanilinocarbonyl)phenyl]-3,4-dihydrocarbostyril (240 mg) as white powder, m.p.: 254°-255° C.

Workup

  1. additionis added
  2. extractionthe mixture is extracted with dichloromethane
  3. washwashed with water
  4. dry with materialdried with magnesium sulfate
  5. distillationThe solvent is distilled off under reduced pressure
  6. customthe resulting residue is crystallized from diethyl ether
  7. customfurther recrystallized from ethanol/diethyl ether/n-hexane

Sources & evidence

ORD record
ord-36782bbd8e7c4353938c251df5e10a9d
Source dataset
uspto-grants-1997_07
Patent number
US05652247

Reaction notes

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