HCID 15087820, compound → 4,6-Dimethylpyridine-2,5-diamine

HRID 1073179Notes

Reaction equation

HRID 1073179 reaction equation
[CH3:1][C:2]1[C:7]([N:8]=NC2C=CC=CC=2)=[C:6]([CH3:16])[N:5]=[C:4]([NH2:17])[CH:3]=1.[H][H]>[Pd].CO>[CH3:1][C:2]1[C:7]([NH2:8])=[C:6]([CH3:16])[N:5]=[C:4]([NH2:17])[CH:3]=1

Participants

5

Reactant 2

HCID 15087820HCID 15087820, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 150878214,6-Dimethylpyridine-2,5-diamineYield 72.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 7.5 parts of 4,6-dimethyl-5-(phenylazo)-2-pyridinamine and 200 parts of methanol was hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia (97:3 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 3.3 parts (72.8%) of 4,6-dimethyl-2,5-pyridinediamine as a residue (int. 96).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated

Sources & evidence

ORD record
ord-98de2065babd41da93cad764d4cea725
Source dataset
uspto-grants-1990_11
Patent number
US04968684

Reaction notes

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