N-[2,2-bis(methyloxy)ethyl]-6-(methyloxy)-3-nitro-2-pyridinamine → N2-[2,2-Bis(methyloxy)ethyl]-6-(methyloxy)-2,3-pyridinediamine

HRID 657101Notes

Reaction equation

HRID 657101 reaction equation
[CH3:1][O:2][CH:3]([O:17][CH3:18])[CH2:4][NH:5][C:6]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[C:8]([O:15][CH3:16])[N:7]=1>CO.[Pd]>[CH3:18][O:17][CH:3]([O:2][CH3:1])[CH2:4][NH:5][C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[C:8]([O:15][CH3:16])[N:7]=1

Participants

4

Reactant 1

HCID 68812011N-[2,2-bis(methyloxy)ethyl]-6-(methyloxy)-3-nitro-2-pyridinamine

Product 1

HCID 86635355N2-[2,2-Bis(methyloxy)ethyl]-6-(methyloxy)-2,3-pyridinediamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N-[2,2-bis(methyloxy)ethyl]-6-(methyloxy)-3-nitro-2-pyridinamine (2.5 g, 10 mmol) in methanol was hydrogenated at 50 psi for 0.5 h over 10% palladium on charcoal (0.9 g). The mixture was filtered, evaporated, and azeotroped with chloroform affording a dark oil (2.2 g).

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated
  3. customazeotroped with chloroform affording a dark oil (2.2 g)

Sources & evidence

ORD record
ord-646ff2d3a8844fb6b61618b09c994005
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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