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

HRID 587592Notes

Reaction equation

HRID 587592 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-4ea36f665be44a3bb975bd994a310d7d
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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