Hydrochloric Acid → (6,8-Dichloro-2,4-dihydroxyquinolin-3-yl)(phenyl)methanone

HRID 370469Notes

Reaction equation

HRID 370469 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[N+](C1C=CC=CC=1)([O-])=O.[Cl:23][C:24]1[CH:25]=[C:26]2[C:31](=[C:32]([Cl:34])[CH:33]=1)[NH:30][C:29](=[O:35])[CH:28]=[C:27]2[OH:36].Cl>O>[C:1]([C:28]1[C:29](=[O:35])[NH:30][C:31]2[C:26]([C:27]=1[OH:36])=[CH:25][C:24]([Cl:23])=[CH:33][C:32]=2[Cl:34])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 7416NitrobenzeneHCID 6451240Aluminum(III) ChlorideHCID 546956806,8-Dichloro-4-hydroxy-2(1H)-quinolinone

Product 1

HCID 135687075(6,8-Dichloro-2,4-dihydroxyquinolin-3-yl)(phenyl)methanoneYield 65.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Benzoyl chloride (0.93 gram) is added to a mixture of 1.5 grams of anhydrous aluminum chloride and 10 ml of nitrobenzene, the mixture is stirred at room temperature until it becomes uniform, stirred at 105° to 110° C. for eight hours with 1.26 grams of 6,8-dichloro-4-hydroxy-2-quinolone, decomposed with concentrated hydrochloric acid, small amount of water is added thereto, and crystals separated out therefrom are collected by filtration. The crystals are washed with water and then washed with methanol and ether to give 1.2 grams of 3-benzoyl-6,8-dichloro-4-hydroxy-2-quinolone, pale yellow powder, melting point 258° to 259° C.

Workup

  1. additionis added
  2. customcrystals separated
  3. filtrationout therefrom are collected by filtration
  4. washThe crystals are washed with water
  5. washwashed with methanol and ether

Sources & evidence

ORD record
ord-e958c3d4a36345979d15fb506dabea24
Source dataset
uspto-grants-1985_07
Patent number
US04526894

Reaction notes

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