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

HRID 516426

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

Reactant 3

HCID 944Nitric Acid

HCID 1118Sulfuric Acid

HCID 652372,9-Dimethyl-1,10-phenanthroline

Product 1

HCID 3797642,9-Dimethyl-5-nitro-1,10-phenanthroline

Procedure

Specifically, 2,9-dimethyl-1,10-phenanthroline shown by the formula (A) in FIG. 1 is reacted with an acid mixture composed of nitric acid and sulfuric acid to give 5-nitro-2,9-dimethyl-1,10-phenanthroline shown by the formula (B) in FIG. 1. The 5-nitro-2,9-dimethyl-1,10-phenanthroline is then reacted with selenium dioxide to give a dialdehyde compound shown by the formula (C) in FIG. 1. This dialdehyde compound is then oxidized to obtain the compound of the formula (1).

Workup

customis reacted with an acid mixture

Sources & evidence

ORD record: ord-0f59cd525fb64804ac07fb173d4489ac
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09110047B2

Linked notes

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