4-(4-Cyanophenyl)amino-2,6-dimethyl-3-nitropyridine → 3-Amino-4-(4-cyanophenyl)amino-2,6-dimethylpyridine

HRID 1886182Notes

Reaction equation

HRID 1886182 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:15]=[C:14]([CH3:16])[N:13]=[C:12]([CH3:17])[C:11]=2[N+:18]([O-])=O)=[CH:5][CH:4]=1)#[N:2]>ClCCl.C(O)C.[Pd]>[NH2:18][C:11]1[C:12]([CH3:17])=[N:13][C:14]([CH3:16])=[CH:15][C:10]=1[NH:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

5

Reactant 1

HCID 106119434-(4-Cyanophenyl)amino-2,6-dimethyl-3-nitropyridine

Product 1

HCID 107051023-Amino-4-(4-cyanophenyl)amino-2,6-dimethylpyridineYield 94.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(4-cyanophenyl)amino-2,6-dimethyl-3-nitropyridine (5.00 g, 18.6 mmol) in a mixture of dichloromethane (20 ml) and ethanol (100 ml) was hydrogenated at 20° C over 10% palladium on charcoal (500 mg) at 138 kPa (20 p.s.i.) for 3 hours. The catalyst was filtered off and the solvents were removed under reduced pressure to give the title compound as a brown solid (4.20 g, 94%).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-d0d013d005024711a9d333bfad87f298
Source dataset
uspto-grants-1992_09
Patent number
US05149814

Reaction notes

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