Hydrochloric Acid → 5-(Chloroacetyl)-8-hydroxy-2(1H)-quinolinone

HRID 27774Notes

Reaction equation

HRID 27774 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]=[CH:7]2.[Cl:13][CH2:14][C:15](Cl)=[O:16].[Cl-].[Al+3].[Cl-].[Cl-].Cl>[N+](C1C=CC=CC=1)([O-])=O>[Cl:13][CH2:14][C:15]([C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:12])[NH:10]2)=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 972508-hydroxyquinolin-2(1H)-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 132602995-(Chloroacetyl)-8-hydroxy-2(1H)-quinolinone

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent2×

Conditions

Temperature
70 °C

Procedure

2.7 g of 8-hydroxycarbostyril and 37 ml of chloroacetyl chloride were dissolved in 250 ml of nitrobenzene, and 85 g of aluminum chloride was added slowly to the solution. The resulting mixture was then stirred at a temperature of 70° C. for 20 hours. 500 ml of a 10% hydrochloric acid aqueous solution was added to the mixture and nitrobenzene was removed by steam distillation. After allowing the mixture to cool, the precipitated crystals were separated by filtration, washed with 300 ml of hot water and recrystallized from methanol to obtain 14.0 g of 5-chloroacetyl-8-hydroxycarbostyril as light yellow crystals having a melting point of 285°-287° C. (with decomposition).

Workup

  1. customwas removed by steam distillation
  2. temperatureto cool
  3. customthe precipitated crystals were separated by filtration
  4. washwashed with 300 ml of hot water
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-41d1d45c00d0450688c25f8b7fff3c8d
Source dataset
uspto-grants-1980_09
Patent number
US04223137

Reaction notes

Loading…