2,6-Diaminopyridine → HCID 57710474, compound
Reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([S:11]([OH:14])(=[O:13])=[O:12])=[C:4]([NH2:15])[N:3]=1.NC1C(N)=C([N+]([O-])=O)C([N+]([O-])=O)=NC=1.NC1C=CC=C(N)N=1.S(O)(O)(=O)=O.NC1C=CC=C(N)N=1.NC1C=CC=C(N)N=1>OS(O)(=O)=O.O=S(=O)=O>[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([S:11]([OH:14])(=[O:13])=[O:12])=[C:4]([NH2:15])[N:3]=1.[NH2:15][C:4]1[C:5]([S:11]([OH:14])(=[O:12])=[O:13])=[CH:6][CH:7]=[C:2]([NH2:1])[N:3]=1Participants
Procedure
In a second embodiment, the present invention further comprises the composition 2,6-diamino-3-nitropyridine-5-sulfonic acid (DANPS). This is the intermediate formed during the process of the present invention described above, which is undesirable in the diaminodinitropyridine product. 2,6-Diamino-3-nitropyridine-5-sulfonic acid is prepared by dissolving 2,6-diaminopyridine or 2,6-diaminopyridine hemisulfate salt in oleum to form 2,6-diaminopyridine-3-sulfonic acid and treating the resulting solution with one stoichiometric amount of concentrated (98%) nitric acid. The resulting 2,6-diamino-3-nitropyridine-5-sulfonic acid is isolated by slowly drowning the reaction mix in an excess of 20% sulfuric acid followed by filtration, and washing the filter cake with water and 5% aqueous ammonium hydroxide solution and drying. 2,6-Diamino-3-nitropyridine-5-sulfonic acid is useful as a chemical intermediate, for instance as a dye intermediate.
Workup
- customformed during the process of the present invention
Sources & evidence
- ORD record
- ord-43195309b1714c2cb2ff72b852df596d
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08115007B2
Reaction notes
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