Hydrochloric Acid → Methyl 2-oxo-1,2-dihydroquinoline-5-carboxylate

HRID 483159Notes

Reaction equation

HRID 483159 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:14])[NH:9]2)([OH:3])=[O:2].Cl.[CH3:16]O>>[CH3:16][O:2][C:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:14])[NH:9]2)=[O:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 132429962-Hydroxyquinoline-5-carboxylic acid

Product 1

HCID 12503491Methyl 2-oxo-1,2-dihydroquinoline-5-carboxylate

Procedure

2 Grams of 5-carboxycarbostyril was suspended in 100 ml of methanol, and hydrogen chloride gas was saturated by bubbling into this suspension, then the reaction mixture was refluxed for 3 hours. The reaction mixture was concentrated to be reduced one-half volume of its initial value, and the precipitated crystals were collected by filtration. The crystals were purified by a silica gel column chromatography, and recrystallized from methanol-chloroform to obtain 230 mg of 5-methoxycarbonylcarbostyril in the form of colorless powdery product.

Workup

  1. customby bubbling into this suspension
  2. temperaturethe reaction mixture was refluxed for 3 hours
  3. concentrationThe reaction mixture was concentrated
  4. filtrationthe precipitated crystals were collected by filtration
  5. customThe crystals were purified by a silica gel column chromatography
  6. customrecrystallized from methanol-chloroform

Sources & evidence

ORD record
ord-18403833482a4f01b1375365ed9f2138
Source dataset
uspto-grants-1986_03
Patent number
US04578381

Reaction notes

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