Hydrochloric Acid → 4,5-Dioxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid

HRID 1680528Notes

Reaction equation

HRID 1680528 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[CH2:10][CH2:11][CH2:12][C:13](=[O:17])[C:14]=2[C:15]=1[OH:16])=[O:5])C.[OH-].[Na+].Cl>O>[OH:16][C:15]1[C:14]2[C:13](=[O:17])[CH2:12][CH2:11][CH2:10][C:9]=2[N:8]=[CH:7][C:6]=1[C:4]([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178469478HCID 178469478, compound

Product 1

HCID 1785246904,5-Dioxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acidYield 93.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 25 ml of water were added 4.0 g of 4-hydroxy-5,6,7,8-tetrahydro-5-oxo-3-quinolinecarboxylic acid ethyl ester and 2.9 g of sodium hydroxide. The resulting reaction mixture was stirred at 90°-95° C. for 2 hours. After being allowed to cool, the reaction mixture was adjusted to pH 2 with 6 N hydrochloric acid. The crystals so precipitated were separated by filtration, washed with water and ethyl alcohol, and then dried at 120° C. under reduced pressure for 4 hours to obtain a yield of 3.3 g of the desired compound. This compound melted (and decomposed) at 278°-279° C. Its infrared absorption spectrum (KBr tablet) had absorption peaks at 3420, 1740, 1690, 1640, 1500, and 820 cm-1.

Workup

  1. customThe resulting reaction mixture
  2. temperatureto cool
  3. customThe crystals so precipitated
  4. customwere separated by filtration
  5. washwashed with water and ethyl alcohol
  6. customdried at 120° C. under reduced pressure for 4 hours

Sources & evidence

ORD record
ord-1b2af0e32485465da42b3a3b030cf7a4
Source dataset
uspto-grants-1981_06
Patent number
US04273932

Reaction notes

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