Ethyl 2-(5-nitropyridin-2-YL)acetate → Ethyl 2-(5-aminopyridin-2-yl)acetate

HRID 2173323Notes

Reaction equation

HRID 2173323 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:8][CH:9]=1)([O-])=O>CO.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:8][CH:9]=1

Participants

4

Reactant 1

HCID 18670679Ethyl 2-(5-nitropyridin-2-YL)acetate

Product 1

HCID 21876034Ethyl 2-(5-aminopyridin-2-yl)acetate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of ethyl (5-nitropyridin-2-yl)acetate (2.40 g, 11.4 mmol), Raney-Ni (50 mg) in 100 mL of MeOH was stirred at room temperature overnight. The mixture was filtered and concentrated to give ethyl (5-aminopyridin-2-yl)acetate. 1H-NMR (400 MHz, CDCl3) δ 8.03 (s, 1H), 7.06 (dd, J=8.4 Hz, 1H), 6.95 (d, J=8.4 Hz, 1H), 4.15 (q, J=7.2 Hz, 2H), 3.71 (s, 2H), 3.65 (br, 2H), 1.24 (t, J=7.2 Hz, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-2a98b5f0be0c4dcbbaf16100cf8d9b5a
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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