Ethyl 2-(5-nitropyrazin-2-yl)acetate → 2-Pyrazineacetic acid, 5-(hydroxyamino)-, ethyl ester

HRID 2173329Notes

Reaction equation

HRID 2173329 reaction equation
[N+:1]([C:4]1[N:5]=[CH:6][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:8][CH:9]=1)([O-])=[O:2]>CCOC(C)=O.[Pd]>[OH:2][NH:1][C:4]1[N: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 77230650Ethyl 2-(5-nitropyrazin-2-yl)acetate

Product 1

HCID 1362782792-Pyrazineacetic acid, 5-(hydroxyamino)-, ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl (5-nitropyrazin-2-yl)acetate (6.7 g, 31.7 mmol) and Pd/C (1 g, 10%) in 300 mL of EtOAc was stirred at room temperature under hydrogen baloon for 6 hours before filtration. The filtrate was concentrated to afford ethyl [5-(hydroxyamino)pyrazin-2-yl]acetate (incomplete reduction). 1H-NMR (400 MHz, CDCl3) δ ppm 8.35 (s, 1H), 8.05 (s, 1H), 4.17 (q, J=7.2 Hz, 2H), 3.75 (s, 2H), 1.24 (t, J=7.2 Hz, 3H).

Workup

  1. filtrationbefore filtration
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-fd15c920362a49a2b472d0fc73829bed
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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