Ammonia → HCID 18399066, compound

HRID 1019387Notes

Reaction equation

HRID 1019387 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[C:9](=[O:10])O[C:7]([C:16]([OH:18])=[O:17])=[C:6]2[C:19]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=1.[NH3:31]>CO>[C:16]([C:7]1[NH:31][C:9](=[O:10])[C:11]2[C:5]([C:6]=1[C:19]1[CH:20]=[C:21]([O:29][CH3:30])[C:22]([O:27][CH3:28])=[C:23]([O:25][CH3:26])[CH:24]=1)=[CH:4][C:3]([O:2][CH3:1])=[C:13]([O:14][CH3:15])[CH:12]=2)([OH:18])=[O:17]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 10862622HCID 10862622, compound

Product 1

HCID 18399066HCID 18399066, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of a solution of 6,7-dimethoxy-4-(3,4,5-trimethoxyphenyl)-isocoumarin-3-carboxylic acid (the compound obtained in Reference Example 50) (2.4 g) in methanol (50 ml) and a 5.5M solution of ammonia in methanol (50 ml) is stirred at room temperature overnight. The reaction solution is concentrated under reduced pressure to remove the ammonia, and further the solvent is distilled off. The residue thus obtained is extracted with chloroform, and the extract is washed with water, dried, and concentrated under reduced pressure. To the residue is added a 4M solution of hydrogen chloride in ethyl acetate (30 ml), and the mixture is stirred at room temperature overnight. The mixture is concentrated under reduced pressure, and the resulting residue is extracted with chloroform. The extract is washed with water, dried, and concentrated under reduced pressure to give 3-carboxy-6,7-dimethoxy-4-(3,4,5-trimethoxyphenyl)-1(2H)-isoquinolinone (1.89 g) as listed in Table 8.

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. customto remove the ammonia
  3. distillationfurther the solvent is distilled off
  4. customThe residue thus obtained
  5. extractionis extracted with chloroform
  6. washthe extract is washed with water
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. additionTo the residue is added a 4M solution of hydrogen chloride in ethyl acetate (30 ml)
  10. concentrationThe mixture is concentrated under reduced pressure
  11. extractionthe resulting residue is extracted with chloroform
  12. washThe extract is washed with water
  13. customdried
  14. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-82a4492adbac4a859604a690549beb5b
Source dataset
uspto-grants-2002_11
Patent number
US06486155B1

Reaction notes

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