6-Methoxy-3-nitropyridine-2-acetonitrile → 5-methoxy-1H-pyrrolo[3,2-b]pyridine

HRID 2298754Notes

Reaction equation

HRID 2298754 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH2:9][C:10]#N)[C:6]([N+:12]([O-])=O)=[CH:5][CH:4]=1>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[CH:9]=[CH:10][NH:12][C:6]2=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 6395106-Methoxy-3-nitropyridine-2-acetonitrile

Product 1

HCID 53243695-methoxy-1H-pyrrolo[3,2-b]pyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Under a hydrogen pressure of 45 psi, 17.70 g (91.7 mmol) of the compound obtained in Step A and 2.5 g of palladium-on-carbon suspended in 300 ml of ethanol are stirred for 5 hours at room temperature. After filtration over Celite and evaporation, the residue is purified over silica gel (eluant: petroleum ether/ethyl acetate, 4:1) to yield the title product in the form of a brown solid.

Workup

  1. filtrationAfter filtration
  2. customover Celite and evaporation
  3. customthe residue is purified over silica gel (eluant: petroleum ether/ethyl acetate, 4:1)

Sources & evidence

ORD record
ord-f0b106ad5e944e82aaf7dbc3d35b2c71
Source dataset
uspto-grants-2002_12
Patent number
US06495543B1

Reaction notes

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