3-{4-[3-(4-Nitrophenyl)-2-oxo-2H-pyridin-1-ylmethyl]phenyl}propionic acid ethyl ester → 3-{4-[3-(4-Aminophenyl)-2-oxo-2H-pyridin-1-ylmethyl]phenyl}propionic acid ethyl ester

HRID 2218121Notes

Reaction equation

HRID 2218121 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=3)[C:15]2=[O:29])=[CH:9][CH:8]=1)[CH3:2].[H][H]>[Pd].C(O)C>[CH2:1]([O:3][C:4](=[O:30])[CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][N:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=3)[C:15]2=[O:29])=[CH:11][CH:12]=1)[CH3:2]

Participants

5

Reactant 2

HCID 693004653-{4-[3-(4-Nitrophenyl)-2-oxo-2H-pyridin-1-ylmethyl]phenyl}propionic acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 116679603-{4-[3-(4-Aminophenyl)-2-oxo-2H-pyridin-1-ylmethyl]phenyl}propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-{4-[3-(4-Nitrophenyl)-2-oxo-2H-pyridin-1-ylmethyl]phenyl}propionic acid ethyl ester (P7, 300 mg, 0.74 mmol) and palladium on charcoal (30 mg) were stirred at room temperature in ethanol (10 mL) under atmospheric pressure of hydrogen for 3 hours, then the reaction mixture was filtered through celite and concentrated. The crude oil was purified by chromatography on silica gel (50% v/v ethyl acetate in petroleum ether) to afford the title compound as an oil.

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. concentrationconcentrated
  3. customThe crude oil was purified by chromatography on silica gel (50% v/v ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-896fe3090a9040ffa93391188c9fd724
Source dataset
uspto-grants-2008_08
Patent number
US07410984B2

Reaction notes

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