Ethyl 2-(6-nitropyridin-3-yl)acetate → Ethyl 2-(6-aminopyridin-3-yl)acetate

HRID 2173315Notes

Reaction equation

HRID 2173315 reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[N:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 21300451Ethyl 2-(6-nitropyridin-3-yl)acetate

Product 1

HCID 67143734Ethyl 2-(6-aminopyridin-3-yl)acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 10% Pd on carbon (9.21 g, 8.66 mmol) in a solution of the ethyl (6-nitropyridin-3-yl)acetate (36.4 g, 173 mmol) in EtOH (364 mL) was hydrogenated at 20 psi and 25° C. for 2 h. The suspension was filtered through Solka Floc eluting with 200 mL EtOH. The filtrate was concentrated and solvent switched with EtOAc, then concetrated to afford the title compound.

Workup

  1. filtrationThe suspension was filtered through Solka Floc
  2. washeluting with 200 mL EtOH
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ba8e3d423875473dad706205271d7426
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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