1-(2,3-Dihydro-5-nitro-1H-pyrrolo[2,3-b]pyridin-1-yl)ethanone → HCID 66845730, compound

HRID 1804736Notes

Reaction equation

HRID 1804736 reaction equation
[C:1]([N:4]1[C:8]2=[N:9][CH:10]=[C:11]([N+:13]([O-])=O)[CH:12]=[C:7]2[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([N:4]1[C:8]2=[N:9][CH:10]=[C:11]([NH2:13])[CH:12]=[C:7]2[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 137785751-(2,3-Dihydro-5-nitro-1H-pyrrolo[2,3-b]pyridin-1-yl)ethanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 66845730HCID 66845730, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 0.43 g (2.08 mmol) of 1-acetyl-2,3-dihydro-5-nitro-1H-pyrrolo[2,3-b]pyridine (Tetrahedron Lett. 1987, 1589) and 0.044 g of 10% palladium-on-charcoal in 15 mL of ethanol is stirred vigorously for 6 hours at room temperature and under 5 atmospheres of hydrogen. After this time, the suspension is filtered through Celite and the filtrate is concentrated under reduced pressure to give 0.24 g of the expected product in the form of a solid.

Workup

  1. filtrationAfter this time, the suspension is filtered through Celite
  2. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-c1d594c5907041dcb4d7bebf8c60051c
Source dataset
uspto-grants-2013_01
Patent number
US08354425B2

Reaction notes

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