Potassium Carbonate → HCID 10862622, compound

HRID 1019406Notes

Reaction equation

HRID 1019406 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([C:14](=O)[C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:35](C(OCC)=O)[C:36]([O:38]CC)=[O:37]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:10][C:11]=1[O:12][CH3:13])[C:7](=[O:8])[O:9][C:35]([C:36]([OH:38])=[O:37])=[C:14]2[C:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69637Diethyl bromomalonateHCID 10959751HCID 10959751, compound

Product 1

HCID 10862622HCID 10862622, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4,5-dimethoxy-2-(3,4,5-trimethoxybenzoyl)benzoic acid (5 g) in dimethylformamide (50 ral) ard added potassium carbonate (3.72 g) and diethyl bromomalonate (2.48 ml), and the mixture is stirred at room temperature overnight. The mixture is evaporated to remove dimethylformamide, and thereto is added chloroform and water. The chloroform layer is separated, and thereto are added dioxane (80 ml) and conc. hydrochloric acid (80 ml). The mixture is heated under reflux for three hours. The reaction mixture is cooled, and the precipitated crystals are collected by filtration washed with acetone, and dried to give 6,7-dimethoxy-4-(3,4,5-trimethoxyphenyl)isocoumarin-3-carboxylic acid (2.85 g) as listed in Table 57.

Workup

  1. customThe mixture is evaporated
  2. customto remove dimethylformamide
  3. additionis added chloroform and water
  4. customThe chloroform layer is separated
  5. additionare added dioxane (80 ml) and conc. hydrochloric acid (80 ml)
  6. temperatureThe mixture is heated
  7. temperatureunder reflux for three hours
  8. temperatureThe reaction mixture is cooled
  9. filtrationthe precipitated crystals are collected by filtration
  10. washwashed with acetone
  11. customdried

Sources & evidence

ORD record
ord-3e0c853cb1cb4830becddcde29d721fa
Source dataset
uspto-grants-2002_11
Patent number
US06486155B1

Reaction notes

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