Sodium Hydroxide → 6,7-Dimethoxy-2,3-quinolinedicarboxylic acid

HRID 868152Notes

Reaction equation

HRID 868152 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([C:15]([O:17]CC)=[O:16])[C:7]([C:20]([O:22]CC)=[O:21])=[CH:6]2.[OH-].[Na+]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([C:15]([OH:17])=[O:16])[C:7]([C:20]([OH:22])=[O:21])=[CH:6]2

Participants

3

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 133519282,3-Diethyl 6,7-dimethoxy-2,3-quinolinedicarboxylate

Product 1

HCID 139230016,7-Dimethoxy-2,3-quinolinedicarboxylic acidYield 101%

Procedure

A suspension of 26.7 g (80 mmol) of 6,7-dimethoxy-2,3-quinolinedicarboxylic acid, diethyl ester, prepared as described by S. B. Kadin and C. H. Lamphere, J. Org. Chem., 49, 4999 (1984), in 10% sodium hydroxide solution (containing 16 g (400 mmol) of sodium hydroxide) was refluxed for 5 hours. After the filtration of the hot solution, 300 ml of water and subsequently 3N hydrochloric acid were added until the pH reached 1.0. The solids were filtered off by suction, washed thoroughly with water, and dried in vacuo to give 22.4 g of the desired product having a melting point of 264°-266° C.

Workup

  1. customprepared
  2. filtrationAfter the filtration of the hot solution, 300 ml of water and subsequently 3N hydrochloric acid
  3. additionwere added until the pH
  4. filtrationThe solids were filtered off by suction
  5. washwashed thoroughly with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-2ca6c5f208304f53b105b20f054a0c33
Source dataset
uspto-grants-1988_10
Patent number
US04777252

Reaction notes

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