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

HRID 2173312Notes

Reaction equation

HRID 2173312 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>CO.[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 887MethanolSolvent

Procedure

A mixture of ethyl (6-nitropyridin-3-yl)acetate (0.9 g, 4.28 mmol), Pd/C (10%, 0.1 g) in MeOH (50 mL) was stirred for 2 hours under H2 atmosphere at room temperature. The mixture was filtered and concentrated to give ethyl (6-aminopyridin-3-yl)acetate. 1H-NMR (400 MHz, CDCl3) δ 7.93 (s, 1H), 7.38 (dd, J=2.4 Hz, 8.4 Hz, 1H), 6.4 6(d, J=8.4 Hz, 1H), 4.48 (br, 2H), 4.13 (q, J=7.2 Hz, 2H), 3.44 (s, 2H), 1.23 (t, J=7.2 Hz, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-89b58ddc23404a5184d6816a15c64706
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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