6-(Chloroacetyl)quinolin-2(1H)-one → 2-Hydroxyquinoline

HRID 358484Notes

Reaction equation

HRID 358484 reaction equation
ClCC([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH:9]=[CH:8]2)=O>N1C=CC=CC=1>[NH:11]1[C:12]2[C:7](=[CH:6][CH:5]=[CH:14][CH:13]=2)[CH:8]=[CH:9][C:10]1=[O:15]

Participants

3

Reactant 1

HCID 128335076-(Chloroacetyl)quinolin-2(1H)-one

Product 1

HCID 60382-Hydroxyquinoline

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

60 Grams of 6-(α-chloroacetyl)carbostyril was suspended in 0.5 kg of pyridine and stirred at 80°-90° C. for 2 hours, then the suspension was stirred under ice-cooling for 1 hour. The crystals thus precipitated were collected by filtration and recrystallized from methanol to obtain 70 g of 6-(α-pyridiniumacetyl)carbostyril chloride 1/2-hydrate in the form of colorless needle-like crystals. Melting point: over 300° C.

Workup

  1. stirringthe suspension was stirred under ice-
  2. temperaturecooling for 1 hour
  3. customThe crystals thus precipitated
  4. filtrationwere collected by filtration
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-c032f0f40eef46ae91a1e2baf1699457
Source dataset
uspto-grants-1984_08
Patent number
US04468402

Reaction notes

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