HCID 22485624, compound → HCID 22485474, compound

HRID 2181301Notes

Reaction equation

HRID 2181301 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)=[N:8][CH:9]=1)([O-])=O>CO.C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[C:12]([O:20][CH3:21])[C:13]([O:18][CH3:19])=[C:14]([O:16][CH3:17])[CH:15]=2)=[N:8][CH:9]=1

Participants

4

Reactant 1

HCID 22485624HCID 22485624, compound

Product 1

HCID 22485474HCID 22485474, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 5-nitro-2-(3,4,5-trimethoxyphenyl)-pyridine (1.50 g, 5.17 mmol) in methanol-ethyl acetate (1:4, 50 mL) was added 10% palladium on charcoal (158.6 mg), and the resulting mixture was stirred at 45° C. for 2 hours and 30 minutes under hydrogen. Insoluble materials were removed by filtration through Celite, and the filtrate was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to yield the title compound as colorless needles (melting point: 153.5-155.5° C. )(1.25 g, yield: 93%).

Workup

  1. customInsoluble materials were removed by filtration through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-2cc95963870e4acd96ec823d92a7b0fa
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

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