HCID 13533221, compound → 5-(Chloroacetyl)-8-hydroxy-2(1H)-quinolinone

HRID 2397555Notes

Reaction equation

HRID 2397555 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>[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

3

Reactant 1

HCID 13533221HCID 13533221, compound

Product 1

HCID 132602995-(Chloroacetyl)-8-hydroxy-2(1H)-quinolinoneYield 85.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

1.7 g of the 5-chloroacetyl-8-chloroacetoxycarbostyril (VI) obtained in Example 5 was added to 50 ml of 10% aqueous hydrochloric acid followed by stirring at 95° to 100° C. for 2 hours. After cooling, the precipitated crystals were filtered, washed with water and then recrystallized from methanol to obtain 1.1 g of 5-chloroacetyl-8-hydroxycarbostyril (IV) having a melting point of 285°-286° C. (with decomposition) as pale yellow crystals.

Workup

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

Sources & evidence

ORD record
ord-eb936fa27ae641498e89a89214ab460d
Source dataset
uspto-grants-1977_05
Patent number
US04022776

Reaction notes

Loading…