Hydrochloric Acid → 2-Quinolone-3-carboxylic acid

HRID 483169

Reaction equation

HRID 483169 reaction equation
[C:1]([OH:7])(=O)[CH2:2][C:3]([OH:5])=[O:4].[NH2:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=O.N1CCCCC1.Cl>N1C=CC=CC=1>[C:3]([C:2]1[C:1](=[O:7])[NH:8][C:9]2[C:10]([CH:11]=1)=[CH:13][CH:14]=[CH:15][CH:16]=2)([OH:5])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 682552-Aminobenzaldehyde

Product 1

HCID 3324882-Quinolone-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

2 Grams of malonic acid was dissolved in 15 ml of pyridine, then 1.2 g of o-aminobenzaldehyde and 2 ml of piperidine were added thereto, and the mixture was stirred at 90° C. for 5 hours. The reaction mixture was poured in an aqueous solution of hydrochloric acid and the crystals precipitated were collected by filtration. Recrystallized from methanol-chloroform to obtain 1.2 g of 3-carboxycarbostyril in the form of colorless needle-like crystals.

Workup

  1. customthe crystals precipitated
  2. filtrationwere collected by filtration
  3. customRecrystallized from methanol-chloroform

Sources & evidence

ORD record
ord-52214a6f88644e678f2d596262547df5
Source dataset
uspto-grants-1986_03
Patent number
US04578381

Linked notes

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