HCID 17405231, compound → HCID 18673880, compound

HRID 1635976Notes

Reaction equation

HRID 1635976 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][CH:12]=2)=[N:8][CH:9]=1)([O-])=O.C(OCC)(=O)C.CCCCCC>C(OCC)(=O)C.[C].[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([OH:19])[CH3:18])=[CH:13][CH:12]=2)=[N:8][CH:9]=1

Participants

5

Reactant 2

HCID 17405231HCID 17405231, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 18673880HCID 18673880, compoundYield 2.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

8.14 g of 1-{4-[(5-nitro-2-pyridinyl)oxy]phenyl}-1-ethanone was dissolved in 15 ml of ethyl acetate and, after adding 2 g of 10% palladium-carbon, the mixture was stirred at 0° C. under partial hydrogen pressure overnight. After the completion of the reaction, the reaction solution was filtered with celite and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography. The compound synthesized in Reference Example 24 was obtained from a fraction prepared by using an eluent (ethyl acetate/n-hexane (2:1)), whereas, the titled compound (193 mg) was obtained from a fraction prepared by using an eluent (ethyl acetate/n-hexane (3:1)).

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe reaction solution was filtered with celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel chromatography
  5. customThe compound synthesized in Reference Example 24
  6. customwas obtained from a fraction
  7. customprepared

Sources & evidence

ORD record
ord-f5572c327fa641dc9136cedd8b34397d
Source dataset
uspto-grants-2003_01
Patent number
US06511995B1

Reaction notes

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