Nitric Acid → 2,9-Dimethyl-5-nitro-1,10-phenanthroline

HRID 257614

Reaction equation

[CH3:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]3[C:10](=[CH:11][CH:12]=2)[CH:9]=[CH:8][C:7]([CH3:16])=[N:6]3)[N:3]=1.[N+:17]([O-])([OH:19])=[O:18]>S(=O)(=O)(O)O>[N+:17]([C:11]1[CH:12]=[C:13]2[C:4]([N:3]=[C:2]([CH3:1])[CH:15]=[CH:14]2)=[C:5]2[C:10]=1[CH:9]=[CH:8][C:7]([CH3:16])=[N:6]2)([O-:19])=[O:18]

Participants

Conditions

Temperature: 100 °C

Procedure

2,9-Dimethyl-1,10-phenanthroline (h) (20 g) was dissolved in a mixture of sulfuric acid (120 ml) and nitric acid (40 ml), and the mixture was heated at 100° C. for 12 hours with stirring. The resulting solution was poured into ice water (300 ml), and the formed precipitate was collected. The precipitate was dissolved in water (500 ml) and neutralized with sodium hydroxide. The resulting precipitate was collected and recrystallized from methanol (300 ml) to give the desired 5-nitro-2,9-dimethyl-1,10-phenanthroline (i) (yield=8.8 g).

Workup

customthe formed precipitate was collected
dissolutionThe precipitate was dissolved in water (500 ml)
customThe resulting precipitate was collected
customrecrystallized from methanol (300 ml)

Sources & evidence

ORD record: ord-5decf9e2f16549c0a64c2625484c21b4
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05262526

Linked notes

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