Acetic Acid → HCID 178497450, compound
Reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[NH:9]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2[C:20]([OH:22])=[O:21])[C:12](=O)[C:10]1=O.O.[C:24](O)(=O)C>>[CH:3]1[CH:4]=[CH:5][CH:6]=[C:1]2[C:2]=1[N:7]=[C:12]1[C:14]3[C:19](=[C:18]([C:20]([O:22][CH3:24])=[O:21])[CH:17]=[CH:16][CH:15]=3)[N:9]=[C:10]1[NH:8]2Participants
Procedure
A suspension of 3.96 g of 1,2-phenylenediamine and 7.00 g of 7-isatincarboxylic acid in 70 ml of acetic acid was heated under reflux for an hour. After completion of the reaction, the reaction solution was allowed to cool to room temperature, followed by addition of water, and resulting precipitate was collected by filtration. The thus obtained 7-indolo[2,3-b]quinolinecarboxylic acid and 170 ml of thionyl chloride were refluxed for 2 hours, and the excess thionyl chloride was evaporated. The residue, after addition of 250 ml of methanol, was stirred overnight. After addition of water, the resulting precipitate was collected by filtration, and purified by silica gel column chromatography to give methyl 7-indolo[2,3-b]quinoxalinecarboxylate.
Workup
- temperaturewas heated
- temperatureunder reflux for an hour
- customAfter completion of the reaction
- customresulting precipitate
- filtrationwas collected by filtration
- temperatureThe thus obtained 7-indolo[2,3-b]quinolinecarboxylic acid and 170 ml of thionyl chloride were refluxed for 2 hours
- customthe excess thionyl chloride was evaporated
- additionThe residue, after addition of 250 ml of methanol
- additionAfter addition of water
- filtrationthe resulting precipitate was collected by filtration
- custompurified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-b58639675db34ffdab3248753c9d6114
- Source dataset
- uspto-grants-1997_01
- Patent number
- US05597921
Reaction notes
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