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

HRID 1153979Notes

Reaction equation

HRID 1153979 reaction equation
ClCC([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[NH:13][C:12](=[O:15])[CH:11]=[CH:10]2)=O>N1C=CC=CC=1>[NH:13]1[C:14]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:12]1=[O:15]

Participants

3

Reactant 1

HCID 132429998-(Chloroacetyl)quinolin-2(1H)-one

Product 1

HCID 60382-Hydroxyquinoline

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

30 Grams of 8-chloroacetylcarbostyril was mixed with 300 ml of pyridine and stirred at 80°-90° C. for 2.5 hours under heating. Then the reaction mixture was ice-cooled and crystals formed were collected by filtration and washed with ether. Recrystallized from methanol to obtain 40.85 g of 8-(α-pyridiniumacetyl)carbostyril chloride 1/2-hydrate. Colorless needle-like crystals. Melting point: 261.5°-264.0° C. (decomposed)

Workup

  1. temperatureunder heating
  2. temperaturecooled
  3. customcrystals formed
  4. filtrationwere collected by filtration
  5. washwashed with ether
  6. customRecrystallized from methanol

Sources & evidence

ORD record
ord-1afd72b284794721abedef3940f35dd5
Source dataset
uspto-grants-1984_12
Patent number
US04487772

Reaction notes

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