(RS)-ethoxy-(3-nitro-2-oxo-2H-pyridin-1-yl)-acetic acid ethyl ester → (RS)-(3-amino-2-oxo-2H-pyridin-1-yl)-ethoxy-acetic acid ethyl ester

HRID 1828094Notes

Reaction equation

HRID 1828094 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH:5]([O:16][CH2:17][CH3:18])[N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[C:7]1=[O:15])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:19])[CH:5]([N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH2:12])[C:7]1=[O:15])[O:16][CH2:17][CH3:18])[CH3:2]

Participants

4

Reactant 1

HCID 86598841(RS)-ethoxy-(3-nitro-2-oxo-2H-pyridin-1-yl)-acetic acid ethyl ester

Product 1

HCID 69641593(RS)-(3-amino-2-oxo-2H-pyridin-1-yl)-ethoxy-acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred suspension of (RS)-ethoxy-(3-nitro-2-oxo-2H-pyridin-1-yl)-acetic acid ethyl ester (3.91 g) at r.t. in ethanol (25 ml) under an argon atmosphere was added 10% Pd/C (215 mg). The reaction mixture was then stirred at r.t. under a hydrogen atmosphere for 16 h. The catalyst was filtered off on a celite pad and washed with ethanol. The filtrate was concentrated. The crude product was purified by chromatography (silica gel, cyclohexane=>cyclohexane/EtOAc 2:3) to give (RS)-(3-amino-2-oxo-2H-pyridin-1-yl)-ethoxy-acetic acid ethyl ester as yellow oil. MS 241.2 ([M+H]+)

Workup

  1. filtrationThe catalyst was filtered off on a celite pad
  2. washwashed with ethanol
  3. concentrationThe filtrate was concentrated
  4. customThe crude product was purified by chromatography (silica gel, cyclohexane=>cyclohexane/EtOAc 2:3)

Sources & evidence

ORD record
ord-f1b057a7c1cb436d8c0a3546c738e9bb
Source dataset
uspto-grants-2006_06
Patent number
US07056932B2

Reaction notes

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