HCID 70665295, compound → HCID 65810177, compound

HRID 333548Notes

Reaction equation

HRID 333548 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N+:16]([O-])=O)[C:5]([NH:8][C:9]2[CH:10]=[C:11]([CH3:15])[CH:12]=[CH:13][CH:14]=2)=[N:6][CH:7]=1>[Pd].C(O)C.C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([NH2:16])[C:5]([NH:8][C:9]2[CH:10]=[C:11]([CH3:15])[CH:12]=[CH:13][CH:14]=2)=[N:6][CH:7]=1

Participants

5

Reactant 1

HCID 70665295HCID 70665295, compound

Product 1

HCID 65810177HCID 65810177, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Palladium on carbon (10%, 1.55 g, 1.456 mmol) was added to a Parr Hydrogenator bottle. The bottle was purged with nitrogen. Then, 5-methyl-3-nitro-N-(m-tolyl)pyridin-2-amine (15.5 g, 63.7 mmol) in 90 mL of ethanol and 90 mL of THF was added. The material was hydrogenated overnight on a Parr Hydrogenator. The mixture was filtered through Celite® to remove the palladium on carbon. The Celite® pad was washed with dichloromethane and evaporated to a solid (13.5 g, 99%).

Workup

  1. customThe bottle was purged with nitrogen
  2. filtrationThe mixture was filtered through Celite®
  3. customto remove the palladium on carbon
  4. washThe Celite® pad was washed with dichloromethane
  5. customevaporated to a solid (13.5 g, 99%)

Sources & evidence

ORD record
ord-a12aee773ac445ec88c2c42b35b1d4de
Source dataset
uspto-grants-2014_11
Patent number
US08883322B2

Reaction notes

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