Hydrochloric Acid → 6-methoxy-2-methylquinoline-3,4-dicarboxylic acid

HRID 1703057Notes

Reaction equation

HRID 1703057 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]2=O.[OH-:14].[K+].C([O:18][C:19](=[O:24])[CH2:20][C:21]([CH3:23])=O)C.Cl>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:21]([CH3:23])[C:20]([C:19]([OH:24])=[O:18])=[C:6]2[C:7]([OH:12])=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8868Ethyl AcetoacetateHCID 14797Potassium HydroxideHCID 383335-Methoxyisatin

Product 1

HCID 3268006-methoxy-2-methylquinoline-3,4-dicarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 59.4 g (0.335 mole) of 5-methoxyisatin, 225 g KOH in 800 ml H2O was treated dropwise with 121.4 g (0.932 mole) of ethylacetoacetate at 55° over a 2 hour period. The solution was refluxed 45 minutes and stirred 2 days at room temperature. Acidification with 300 ml concd. HCl while maintaining the temperature at ambient conditions gave a tan solid that was filtered, washed with H2O and dried; yield 60.8 g (69.4%).

Workup

  1. temperatureThe solution was refluxed 45 minutes
  2. customgave a tan solid
  3. filtrationthat was filtered
  4. washwashed with H2O
  5. customdried

Sources & evidence

ORD record
ord-8d1fe819861c4aeba22540e563fb154a
Source dataset
uspto-grants-1982_09
Patent number
US04350814

Reaction notes

Loading…