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

HRID 2397556Notes

Reaction equation

HRID 2397556 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]([O:15]C(=O)CCl)=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:20])[NH:10]2)=[O:4].Cl>[OH-].[K+]>[Cl:1][CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:20])[NH:10]2)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13533221HCID 13533221, compound

Product 1

HCID 132602995-(Chloroacetyl)-8-hydroxy-2(1H)-quinolinoneYield 89.9%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

2.5 g of the 5-chloroacetyl-8-chloroacetoxycarbostyril (VI) obtained in Example 5 was added to 30 ml of 5% aqueous potassium hydroxide followed by stirring at 20° to 25° C. for 30 minutes. The resulting solution was adjusted to a pH of 2 to 3 with diluted hydrochloric acid while cooling. The precipitated crystals were filtered, washed with water and recrystallized from methanol to obtain 1.7 g of 5-chloroacetyl-8-hydroxycarbostril (IV) having a melting point of 285°-287° C. (with decomposition) as pale yellow crystals.

Workup

  1. temperaturewhile cooling
  2. filtrationThe precipitated crystals were filtered
  3. washwashed with water
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-8e1e9a049dd3469187d09f07108e0d8f
Source dataset
uspto-grants-1977_05
Patent number
US04022776

Reaction notes

Loading…