HCID 12774644, compound → HCID 12774652, compound

HRID 848768Notes

Reaction equation

HRID 848768 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][C:6]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[CH:5][N:4]=1>[Pd].C(O)C>[CH3:1][NH:2][C:3]1[N:4]=[CH:5][C:6]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[CH:7][C:8]=1[NH2:9]

Participants

4

Reactant 1

HCID 12774644HCID 12774644, compound

Product 1

HCID 12774652HCID 12774652, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture containing 21 g. of 2-methylamino-3-nitro-5-(4-pyridinyl)pyridine, 200 ml. of ethanol and 2 g. of 10% palladium-on-charcoal was shaken under catalytic hydrogenation conditions in a Parr apparatus at room temperature for three hours. The reaction mixture was filtered and the solvent distilled off in vacuo. The remaining solid was recrystallized from acetonitrile, washed with ether and dried in vacuo at 70° C. to yield 3-amino-2-methylamino-5-(4-pyridinyl)pyridine (alternatively named N6 -methyl-[3,4'-bipyridine]-5,6-diamine), m.p. 184°-187° C.

Workup

  1. additionA mixture containing 21 g
  2. filtrationThe reaction mixture was filtered
  3. distillationthe solvent distilled off in vacuo
  4. customThe remaining solid was recrystallized from acetonitrile
  5. washwashed with ether
  6. customdried in vacuo at 70° C.

Sources & evidence

ORD record
ord-6d57d7a5bf494144a792661046693127
Source dataset
uspto-grants-1981_10
Patent number
US04297360

Reaction notes

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