Methanol → 2-Ethyl-4-{[6-(methylsulfonyl)pyridin-3-yl]oxy}aniline

HRID 1042133Notes

Reaction equation

HRID 1042133 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:19]=1[N+:20]([O-])=O)[O:6][C:7]1[CH:8]=[CH:9][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[N:11][CH:12]=1)=[CH2:2].O1CCCC1.CO.C(OCC)(=O)C>[C].[Pd].CCCCCC>[CH2:1]([C:3]1[CH:4]=[C:5]([O:6][C:7]2[CH:12]=[N:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[CH:17]=[CH:18][C:19]=1[NH2:20])[CH3:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 667261635-(3-Ethenyl-4-nitrophenoxy)-2-(methylsulfonyl)pyridine

Product 1

HCID 667259082-Ethyl-4-{[6-(methylsulfonyl)pyridin-3-yl]oxy}anilineYield 89%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8058HexaneSolvent

Procedure

A mixture of 5-(3-ethenyl-4-nitrophenoxy)-2-(methylsulfonyl)pyridine (5.0 g), 10% palladium carbon (1.0 g, containing water (50%)), tetrahydrofuran (100 mL), and methanol (50 mL) was stirred under a hydrogen atmosphere (balloon pressure) at room temperature for 3 days. The catalyst was filtered off, and the obtained filtrate was concentrated under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (ethyl acetate:hexane=25:75 to 60:40, volume ratio) to give the title compound (4.05 g, yield 89%) as a pale-yellow oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe obtained filtrate was concentrated under reduced pressure
  3. customThe obtained crude product

Sources & evidence

ORD record
ord-331b2f12c43c46b8b3956d9b073161f4
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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