8-Hydroxyquinoline → 1-(8-Hydroxyquinolin-5-yl)ethan-1-one--hydrogen chloride (1/1)

HRID 883625Notes

Reaction equation

HRID 883625 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[C:12]([Cl:15])(=[O:14])[CH3:13].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)CCl>[ClH:15].[C:12]([C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2)(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 19238-HydroxyquinolineHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 200268801-(8-Hydroxyquinolin-5-yl)ethan-1-one--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

8-hydroxyquinoline (500 gms/3.44 moles) was dissolved in ethylene chloride (5 lits) at 25-30° C. in an inert atmosphere. To this solution was added acetyl chloride (260 ml/4.12 moles) drop wise in 2 hours. The reaction mass was stirred for 15-20 minutes. Then, aluminum chloride (1.15 Kg/8.62 moles) was added in lots in 2 hours. The reaction mass was stirred at 25-30° C. for 15-20 minutes and heated to 70° C. for 13-14 hours. After completion of reaction, the reaction mass was cooled to 25-30° C. and slowly quenched in a mixture of crushed ice (10 Kg) and conc. HCl (500 ml). The resulting slurry was stirred for 15-20 minutes. The crude 5-acetyl-8-hydroxyquinoline hydrochloride was isolated by filtration, washed with 2 liters of acetone and dried under vacuum for 1 hour. Yield: 680 gms.

Workup

  1. stirringThe reaction mass was stirred at 25-30° C. for 15-20 minutes
  2. customAfter completion of reaction
  3. temperaturethe reaction mass was cooled to 25-30° C.
  4. customslowly quenched in a mixture of crushed ice (10 Kg) and conc. HCl (500 ml)
  5. stirringThe resulting slurry was stirred for 15-20 minutes

Sources & evidence

ORD record
ord-3f9312febbfd47ddb93d8b9e3342d2c0
Source dataset
uspto-grants-2012_08
Patent number
US08236959B2

Reaction notes

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