1,4-Dioxane → 6-Methyl-2,4-bis-methylsulfanylpyridin-3-ylamine

HRID 2257189Notes

Reaction equation

HRID 2257189 reaction equation
[N+:1]([C:4]1[C:5]([S:13][CH3:14])=[N:6][C:7]([CH3:12])=[CH:8][C:9]=1[S:10][CH3:11])([O-])=O.O1CCOCC1.[H][H]>[Ni].CO>[NH2:1][C:4]1[C:5]([S:13][CH3:14])=[N:6][C:7]([CH3:12])=[CH:8][C:9]=1[S:10][CH3:11]

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 100368396-methyl-2,4-bis(methylthio)-3-nitroPyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 99903926-Methyl-2,4-bis-methylsulfanylpyridin-3-ylamineYield 85%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 18.9 g (0.082 mol) 3-nitro-2,4-bis(methylthio)-6-methylpyridine and 18.9 g Raney nickel in 600 ml. 1,4-dioxane and 300 ml methanol was shaken with hydrogen (15 psi) in a Parr hydrogenation apparatus for 3.5 hr. The catalyst was filtered and the filtrate was concentrated to dryness in vacuo. The solid residue was chromatographed on silica gel (650 g), eluting with 9:1 hexane/ethyl acetate to yield 14.0 g. (85% yield) of the title compound as an off-white solid.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated to dryness in vacuo
  3. customThe solid residue was chromatographed on silica gel (650 g)
  4. washeluting with 9:1 hexane/ethyl acetate
  5. customto yield 14.0 g

Sources & evidence

ORD record
ord-f08ac9529c584721afd878b7484cd6df
Source dataset
uspto-grants-1997_08
Patent number
US05656634

Reaction notes

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