2-Methoxy-5-Nitro-6-(2-Dimethylaminoethen-1-yl)pyridine → 5-methoxy-1H-pyrrolo[3,2-b]pyridine

HRID 277989Notes

Reaction equation

HRID 277989 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+]([O-])=O)=[C:5]([CH:12]=[CH:13][N:14](C)C)[N:4]=1.[H][H]>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:6](=[CH:7][CH:8]=1)[NH:14][CH:13]=[CH:12]2

Participants

5

Reactant 2

HCID 544306472-Methoxy-5-Nitro-6-(2-Dimethylaminoethen-1-yl)pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 53243695-methoxy-1H-pyrrolo[3,2-b]pyridineYield 76.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Methoxy-5-Nitro-6-(2-Dimethylaminoethen-1-yl)pyridine (38.78 g, 174 mmol) was dissolved in 1.2 L of ethanol, and charged with 10% palladium on carbon (5.0 g). The mixture was hydrogenated at room temperature under 40 p.s.i. of hydrogen pressure for 4 hours. After filtration through celite followed by chromatography on silica gel (50% ethyl acetate/hexane), the material was recrystallized from ethyl acetate/hexane to provide 19.62 g of the title compound. (76%). MS(m/e): 149 (M+). EA calculated for C8H8N2O: C, 64.85; H, 5.44; N, 18.91. Found: C, 64.72; H, 5.33; N, 18.76.

Workup

  1. customwas hydrogenated at room temperature under 40 p.s.i
  2. filtrationAfter filtration through celite
  3. customthe material was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-4b786728fb5c4954904e3541e701b874
Source dataset
uspto-grants-2002_03
Patent number
US06358972B1

Reaction notes

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