Ethyl 2-[(3-nitropyridin-2-YL)amino]acetate → Ethyl 2-(3-aminopyridin-2-ylamino)acetate

HRID 82678Notes

Reaction equation

HRID 82678 reaction equation
[N+:1]([C:4]1[C:5]([NH:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O>[Pd].CCOC(C)=O>[NH2:1][C:4]1[C:5]([NH:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 14062544Ethyl 2-[(3-nitropyridin-2-YL)amino]acetate

Product 1

HCID 14390203Ethyl 2-(3-aminopyridin-2-ylamino)acetateYield 79.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl N-(3-nitropyridin-2-yl)glycinate (26 g) and 10% palladium on carbon (50% wet, 7.3 g) in AcOEt (250 mL) was hydrogenated under balloon pressure at room temperature for 8 h. The catalyst was removed by filtration. To the filtrate were added triethylamine (5.0 mL) and 10% palladium on carbon (50% wet, 7.3 g). The mixture was hydrogenated under balloon pressure at room temperature overnight. The mixture was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, eluted with 10%-50% AcOEt in hexane) to give the title compound (18 g).

Workup

  1. customThe catalyst was removed by filtration
  2. additionTo the filtrate were added triethylamine (5.0 mL) and 10% palladium on carbon (50% wet, 7.3 g)
  3. waitThe mixture was hydrogenated under balloon pressure at room temperature overnight
  4. concentrationThe mixture was concentrated under reduced pressure
  5. customThe residue was purified by column chromatography (silica gel, eluted with 10%-50% AcOEt in hexane)

Sources & evidence

ORD record
ord-5b0cb30521f24f6e81dd57617dd91c71
Source dataset
uspto-grants-2014_09
Patent number
US08846713B2

Reaction notes

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