Acetic Acid → HCID 21442884, compound

HRID 328573Notes

Reaction equation

HRID 328573 reaction equation
[Cl:1][O-].[Na+].[C:4]([C:7]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[N:12]2)(=[O:6])[CH3:5].C(O)(=O)C>CO.O>[C:4]([C:7]1[CH:16]=[C:15]([Cl:1])[C:14]([OH:17])=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[N:12]2)(=[O:6])[CH3:5]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 95877QuinacetolHCID 23665760Sodium Hypochlorite

Product 1

HCID 21442884HCID 21442884, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

350 ml of a 14% strength sodium hypochlorite solution are added dropwise to a suspension of 94 g of 5-acetyl-8-hydroxyquinoline in 1 litre of methanol and 1 litre of water at 10°-20°C, whilst stirring well. After stirring for a further hour, the mixture is acidified with 60 ml of glacial acetic acid and diluted with 1 liter of water, and the product is filtered off. The filter residue is washed with water and recrystallised, whilst still moist, from alcohol. 70 g of almost colourless 5-acetyl-7-chloro-8-hydroxyquinoline are obtained, melting point 163°-166° C.

Workup

  1. stirringAfter stirring for a further hour
  2. filtrationthe product is filtered off
  3. washThe filter residue is washed with water
  4. customrecrystallised

Sources & evidence

ORD record
ord-22e43008f29540f5896f1b36fc4ee8a4
Source dataset
uspto-grants-1977_04
Patent number
US04017627

Reaction notes

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