Water → 6-Chloro-5-hydroxy-3,4-dihydrocarbostyril

HRID 621546Notes

Reaction equation

HRID 621546 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:12])[NH:7]2.[Cl:13]Cl.O>C(O)(=O)C>[Cl:13][C:11]1[C:2]([OH:1])=[C:3]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:12])[CH2:5][CH2:4]2

Participants

5

Reactant 3

HCID 962WaterHCID 24526ChlorineHCID 1691533,4-Dihydro-5-hydroxy-2(1H)-quinolinone

Product 1

HCID 128994166-Chloro-5-hydroxy-3,4-dihydrocarbostyrilYield 69.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

16.4 grams of 5-hydroxy-3,4-dihydrocarbostyril are dissolved in 300 ml of acetic acid. This solution is stirred at room temperature, and 50 ml of acetic acid solution containing 7 g of chlorine are added dropwise and the reaction is continued for 3 hours with stirring. The reaction mixture is poured into 500 ml of water and allowed to stand for 1 hour and the precipitate thus formed is separated by filtration, washed with water and then dried. Recrystallization from ethanol-water obtains 13.5 g of 6-chloro-5-hydroxy-3,4-dihydrocarbostyril in the form of colorless needle-like crystals with a melting point of 209°-210° C.

Workup

  1. additionare added dropwise
  2. stirringwith stirring
  3. waitto stand for 1 hour
  4. customthe precipitate thus formed
  5. customis separated by filtration
  6. washwashed with water
  7. customdried
  8. customRecrystallization from ethanol-water

Sources & evidence

ORD record
ord-dc1dd8cf247140d38e9cce63372c1a6f
Source dataset
uspto-grants-1989_04
Patent number
US04824840

Reaction notes

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