Hydrochloric Acid → 2-Oxo-1,2,3,4-tetrahydroquinoline-3-carboxylic acid

HRID 2269717Notes

Reaction equation

HRID 2269717 reaction equation
[OH-].[Na+].[O:3]=[C:4]1[CH:13]([C:14]([O:16]C)=[O:15])[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5]1.Cl>C1COCC1.CO>[O:3]=[C:4]1[CH:13]([C:14]([OH:16])=[O:15])[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18333017HCID 18333017, compound

Product 1

HCID 133204612-Oxo-1,2,3,4-tetrahydroquinoline-3-carboxylic acidYield 90.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1N Aqueous sodium hydroxide solution (80 ml) was added dropwise to the mixed solution of methyl 2-oxo-1,2,3,4-tetrahydro-3-quinolinecarboxylate (8.322 g) in THF (80 ml) and methanol (80 ml) at 0° C. The reaction mixture was stirred at room temperature for 4 hours. 1N Hydrochloric acid (90 ml) was added dropwise to the reaction mixture at 0° C., which was then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried and concentrated to obtain crude crystals of the entitled compound (7.032 g). The obtained crude crystals were put to use in the following reaction without purification.

Workup

  1. extractionwhich was then extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0630f82b5193441586db31ac2cfecaed
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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