Sodium Hydroxide → 2-Oxo-1,2,3,4-tetrahydroquinoline-5-carboxylic acid

HRID 483158Notes

Reaction equation

HRID 483158 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].[OH-].[Na+].[H][H]>O.[Pt].[C]>[C:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][C:8](=[O:14])[NH:9]2)([OH:3])=[O:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 132429962-Hydroxyquinoline-5-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 132430022-Oxo-1,2,3,4-tetrahydroquinoline-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 178503042HCID 178503042, compoundCatalystHCID 962WaterSolvent

Procedure

2 Grams of 5-carboxycarbostyril was suspended in 30 ml of water, then 10N-sodium hydroxide aqueous solution was added to dissolve the crystals. To this solution was added 500 mg of 10% platinum-carbon and this mixture was catalytically reduced with hydrogen gas under condition of 3-4 kg/cm2 at 70° C. After the completion of the reaction, the catalyst was removed from the reaction mixture by filtration, then the pH of the filtrate was adjusted to about pH=1 by adding concentrated hydrochloric acid. The precipitated crystals were collected by filtration, recrystallized from methanol to obtain 820 mg of 5-carboxy-3,4-dihydrocarbostyril in the form of colorless needle-like crystals.

Workup

  1. dissolutionto dissolve the crystals
  2. customAfter the completion of the reaction
  3. customthe catalyst was removed from the reaction mixture by filtration
  4. additionby adding concentrated hydrochloric acid
  5. filtrationThe precipitated crystals were collected by filtration
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-ceb630d835aa44c0968e5a661bf75f84
Source dataset
uspto-grants-1986_03
Patent number
US04578381

Reaction notes

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