Dimethylformamide → N-(5-nitropyridin-2-yl) para-phenylenediamine

HRID 1007117Notes

Reaction equation

HRID 1007117 reaction equation
C(N(CC)CC)C.CN(C)C=O.Cl[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=1.Cl.[C:24]1([NH2:31])[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1>O>[N+:20]([C:17]1[CH:18]=[CH:19][C:14]([NH:30][C:27]2[CH:28]=[CH:29][C:24]([NH2:31])=[CH:25][CH:26]=2)=[N:15][CH:16]=1)([O-:22])=[O:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 783082-Chloro-5-nitropyridineHCID 120279p-Phenylenediamine, monohydrochloride

Product 1

HCID 24700317N-(5-nitropyridin-2-yl) para-phenylenediamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triethylamine (35 ml) was added into dimethylformamide (50 ml) including 2-chloro-5-nitropyridine (1) (9.5 g, 60 mmol) and para-phenylenediamine hydrochloride (10.9 g, 60 mmol), and stirred at the room temperature for 14 hours. After the reaction having been completed, the solution was poured into water, and the resultant solid was filtered and then N-(5-nitropyridin-2-yl) para-phenylenediamine was obtained as a brown solid. This solid was dissolved in ethanol (800 ml) and added with 5%-palladium carbon (2 g) so as to cause a hydrogen substitution, and then reduced at 70° C. under the normal pressure for 6 hours. After the reaction having been completed, the celite filtering was applied to remove the palladium carbon, and then it was washed by using a mixed solvent of ethyl acetate and hexane, thus obtained N-(5-amino-pyridin-2-yl) para-phenylenediamine (8.8 g, 75%).

Workup

  1. filtrationthe resultant solid was filtered

Sources & evidence

ORD record
ord-9f3add445076453383401c22a156d5df
Source dataset
uspto-grants-2004_09
Patent number
US06794378B2

Reaction notes

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