Nitric Acid → 1,10-Phenanthroline-5,6-dione
Reaction equation
[OH2:1].[N:2]1[C:15]2[C:6](=[CH:7][CH:8]=[C:9]3[C:14]=2[N:13]=[CH:12][CH:11]=[CH:10]3)[CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[N+]([O-])(O)=O.[OH-:25].[Na+]>>[N:2]1[C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][N:13]=3)[C:8](=[O:1])[C:7](=[O:25])[C:6]=2[CH:5]=[CH:4][CH:3]=1Participants
Procedure
25 g of 1,10-phenanthroline-hydrate was dissolved into 125 ml of 20% fuming sulfuric acid. The sulfuric acid was heated at the temperature of 110° to 125° C., and 33 ml of 72% concentrated nitric acid was added into the sulfuric acid. While the mixed solution was current-circulated at the temperature of 143° C. for 30 minutes, 66 ml of 72% concentrated nitric acid was added into the mixed solution. Then, the mixed solution was stirred for 1.5 hours to promote its reaction. After the reaction, the mixed solution was cooled to the room temperature, and it was poured into an ice. The ice-containing solution was neutralized by adding 30% sodium hydroxide solution. A precipitated by-product, 5-nitro-1,10-phenanthroline was filtered and removed from the neutralized solution. The filtered solution was extracted by chloroform, and the extracted chloroform solution was dried by sodium sulfate anhydride. Furthermore, the dried solution was vacuum-concentrated to obtain a yellow rough crystal of 1,10-phenanthroline-5,6-dione. The rough crystal was purified by recrystallization of ethanol.
Workup
- customits reaction
- customAfter the reaction
- filtrationA precipitated by-product, 5-nitro-1,10-phenanthroline was filtered
- customremoved from the neutralized solution
- extractionThe filtered solution was extracted by chloroform
- dry with materialthe extracted chloroform solution was dried by sodium sulfate anhydride
- concentrationFurthermore, the dried solution was vacuum-concentrated
Sources & evidence
- ORD record
- ord-ca4be4da108b41fdb7b7bfcf1ed8f278
- Source dataset
- uspto-grants-1998_01
- Patent number
- US05710273
Reaction notes
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