Sodium Hydroxide → 2,3-Quinolinedicarboxylic acid

HRID 1650110Notes

Reaction equation

HRID 1650110 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([O:13]CC)=[O:12])[C:2]=1[C:16]([O:18]CC)=[O:17].[OH-].[Na+]>C(O)C.O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([OH:13])=[O:12])[C:2]=1[C:16]([OH:18])=[O:17]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10880272Diethyl 2,3-quinolinedicarboxylate

Product 1

HCID 695082,3-Quinolinedicarboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of diethyl 2,3-quinolinedicarboxylate (0.162 mol) in ethanol (150 ml) is added a solution of sodium hydroxide (0.50 mol) in water (400 ml). The mixture is heated at reflux for 5 hours, and the ethanol then removed by distillation at atmospheric pressure. The solution is cooled in an ice bath, diluted with water (100 ml), and acidified with concentrated hydrochloric acid, added in small increments. The precipitate is filtered, washed with water, and air dried to afford the desired 2,3-quinolinedicarboxylic acid as the trihydrate; mp 271°-277° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 5 hours
  3. customthe ethanol then removed by distillation at atmospheric pressure
  4. temperatureThe solution is cooled in an ice bath
  5. additiondiluted with water (100 ml)
  6. additionadded in small increments
  7. filtrationThe precipitate is filtered
  8. washwashed with water, and air
  9. customdried

Sources & evidence

ORD record
ord-f3a9cc2f57e142d4809da7b740c0121e
Source dataset
uspto-grants-1990_05
Patent number
US04923504

Reaction notes

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