Ammonia → HCID 23084821, compound

HRID 1783304Notes

Reaction equation

HRID 1783304 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:10](=O)[O:9][CH:8]=2)=[CH:3][CH:2]=1.Cl.C(=O)([O-])[O-].[K+].[K+].[NH3:25]>C(O)C>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:10](=[O:9])[NH:25][CH:8]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 23084610HCID 23084610, compound

Product 1

HCID 23084821HCID 23084821, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(Pyridin-4-yl)isocoumarin (4.9 g) was suspended in ethanol and 28% aqueous ammonia, and the mixture was heated under reflux for 1 hr. Concentrated hydrochloric acid was added to acidify the reaction mixture, and the mixture was further stirred at room temperature for 1 hr. After the completion of the reaction, aqueous potassium carbonate solution was added to the reaction mixture, and the mixture was extracted with a mixed solvent (chloroform:methanol=10:1). The organic layer was dried over magnesium sulfate. The solvent was evaporated, and the obtained residue was collected by filtration to give 4-(pyridin-4-yl)-2H-isoquinolin-1-one (2.9 g).

Workup

  1. temperatureunder reflux for 1 hr
  2. additionwas added to the reaction mixture
  3. extractionthe mixture was extracted with a mixed solvent (chloroform:methanol=10:1)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customThe solvent was evaporated
  6. filtrationthe obtained residue was collected by filtration

Sources & evidence

ORD record
ord-13f482487fc84e3b839642656948beb4
Source dataset
uspto-grants-2009_03
Patent number
US07501412B2

Reaction notes

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