N-{2-[(5-nitro-2-pyridinyl)amino]ethyl}acetamide → 2-(2-Acetamidoethylamino)-5-aminopyridine

HRID 1106571Notes

Reaction equation

HRID 1106571 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][NH:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][N:9]=1)(=[O:3])[CH3:2]>C(O)C.O.[Pd]>[C:1]([NH:4][CH2:5][CH2:6][NH:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][N:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 2901081N-{2-[(5-nitro-2-pyridinyl)amino]ethyl}acetamide

Product 1

HCID 181802302-(2-Acetamidoethylamino)-5-aminopyridineYield 43.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 19096565Water ethanolSolvent

Procedure

A suspension of 2-(2-acetamidoethylamino)-5-nitropyridine (4.0 g, 17.86 mmol) in ethanol-water (3:1, 160 ml) was shaken with 10% palladium on charcoal (400 mg) under an atmosphere of hydrogen for 5 h then filtered through Celite™ and the filtrate concentrated. The residue was subjected to column chromatography (silica, 3-10% methanol--CH2Cl2) to afford the title compound (1.52 g) as an air-sensitive deep mauve gum. MS (ES+) 195 (MH+). δH (d6DMSO) 7.89 (1H, br s), 7.45 (1H, d, J 2.5 Hz), 6.82 (1H, dd, J 2.5, 8.7 Hz), 6.28 (1H, d, J 8.7 Hz), 5,60 (1H, br s), 4.34 (2H, br s), 3.16 (4H, m) and 1.79 (3H, s).

Workup

  1. filtrationthen filtered through Celite™
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-f487f36cab854793b677ce67dec3b4e5
Source dataset
uspto-grants-2000_05
Patent number
US06057329

Reaction notes

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