HCID 23153479, compound → HCID 23153051, compound

HRID 492738Notes

Reaction equation

HRID 492738 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[N+:19]([O-])=O)[O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:7]=1>CO.[C].[Pd]>[NH2:19][C:18]1[CH:17]=[CH:16][C:4]([O:5][C:6]2[CH:11]=[CH:10][N:9]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:7]=2)=[CH:3][C:2]=1[F:1]

Participants

4

Reactant 1

HCID 23153479HCID 23153479, compound

Product 1

HCID 23153051HCID 23153051, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 4-(3-fluoro-4-nitrophenoxy)pyridine-2-carboxylate (200 mg) in methanol (40 ml) was added 10% palladium carbon, followed by stirring under a hydrogen atmosphere at room temperature for 4.5 hrs. The reaction mixture was filtered to remove the catalyst, which was then washed with methanol. The filtrate was concentrated under a reduced pressure to give a residue, which was purified by silica gel column chromatography (eluent; ethyl acetate). Fractions containing the target compound were concentrated to provide a crude product of the titled compound (181 mg) as a brown oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst, which
  3. washwas then washed with methanol
  4. concentrationThe filtrate was concentrated under a reduced pressure
  5. customto give a residue, which
  6. customwas purified by silica gel column chromatography (eluent; ethyl acetate)
  7. additionFractions containing the target compound
  8. concentrationwere concentrated

Sources & evidence

ORD record
ord-0ea0bfad7ac743da96e3c26dd6a8f5b3
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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