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

HRID 1502116Notes

Reaction equation

HRID 1502116 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]>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][C:7]1[CH:6]=[N:5][C:4]([NH:1][OH:2])=[CH:9][N:8]=1)[CH3:15]

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-nitropyrazine-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 balloon for 6 hours before filtration. The filtrate was concentrated to afford ethyl[5-(hydroxyamino)pyrazin-2-yl]acetate (incomplete reduction).

Workup

  1. filtrationbefore filtration
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2c705a6d842543e2bc5fee15ebdbe5bd
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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