Hydrochloric Acid → Quinoline-5,6-dicarboxylic acid

HRID 1974664Notes

Reaction equation

HRID 1974664 reaction equation
[N:1]1[C:10]2[C:5](=[C:6]([C:15]([O:17]C)=[O:16])[C:7]([C:11]([O:13]C)=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].CO.Cl>O>[N:1]1[C:10]2[C:5](=[C:6]([C:15]([OH:17])=[O:16])[C:7]([C:11]([OH:13])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 19101917HCID 19101917, compound

Product 1

HCID 19101925Quinoline-5,6-dicarboxylic acidYield 92.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of dimethyl 5,6-quinolinedicarboxylate (2.46 g, 10.0 mmol), aqueous sodium hydroxide (5.0 mL, 5m, 25.0 mmol) and methanol is heated to 80° C., treated with water at 80° C. until the mixture is homogeneous, stirred for 2 hours at reflux temperature, cooled to 0° C., acidified to pH 4 with concentrated hydrochloric acid and filtered. The filter cake is air dried to give the title product as a white powder 2.00 g, 91.7%) mp >360 C, identified by H1NMR spectroscopy.

Workup

  1. temperatureat reflux temperature
  2. temperaturecooled to 0° C.
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-69fcf1a540304ce19a3f391ff82a6960
Source dataset
uspto-grants-1994_02
Patent number
US05283335

Reaction notes

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