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

HRID 1649008Notes

Reaction equation

HRID 1649008 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-].[N+](C1C=CC=CC=1)([O-])=O>Cl>[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 6577Chloroacetyl chlorideHCID 7416NitrobenzeneHCID 972508-hydroxyquinolin-2(1H)-oneHCID 6451240Aluminum(III) Chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 8-hydroxycarbostyril (27 g) and chloroacetyl chloride (37 ml) in ntirobenzene (250 ml) was added aluminum chloride (85 g) portionwise and the mixture was stirred at 70° C. for 20 hours. After adding 10% hydrochloric acid (500 ml), nitrobenzene was removed by steam distillation. After cooling, crystals which formed were collected by filtration, washed with 300 ml of hot water and recrystallized from methanol to give 4.0 g of 5-chloroacetyl-8-hydroxycarbostyril.

Workup

  1. customwas removed by steam distillation
  2. temperatureAfter cooling
  3. customcrystals which formed
  4. filtrationwere collected by filtration
  5. washwashed with 300 ml of hot water
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-9044843f8cda477f8220d25a01ba982a
Source dataset
uspto-grants-1983_11
Patent number
US04414390

Reaction notes

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