Nitrogen → 2-Acetamido-5-aminopyridine

HRID 865673Notes

Reaction equation

HRID 865673 reaction equation
N#N.[C:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][N:8]=1)(=[O:5])[CH3:4].C([O-])=O.[NH4+]>CN(C=O)C.[Pd].CO>[C:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][N:8]=1)(=[O:5])[CH3:4]

Participants

7

Reactant 3

HCID 947NitrogenHCID 3451252-Acetamido-5-nitropyridineHCID 2723923Ammonium formate

Product 1

HCID 27352192-Acetamido-5-aminopyridineYield 88.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A N2 covered solution of 1.19 g (6.6 mmol) of the product from Step 1 in 24 ml of DMF was treated with 2.07 g (32.9 mmol) of ammonium formate followed by 0.36 g of palladium on carbon catalyst. After stirring vigorously at room temperature for 17 hours, the reaction was diluted with MeOH and the catalyst was removed by filtration through celite. The filtrate was concentrated in vacuo and the residue was chromatographed over silica gel (3% MeOH: 0.3% NH4OH: CH2Cl2) to yield 0.876 g, m.p. 152°-153.5° C. (88.2%) of the titled product.

Workup

  1. customthe catalyst was removed by filtration through celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was chromatographed over silica gel (3% MeOH: 0.3% NH4OH: CH2Cl2)

Sources & evidence

ORD record
ord-96c5e8a930fb438ebc8d061ffae6a959
Source dataset
uspto-grants-1996_10
Patent number
US05567722

Reaction notes

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