Pyridine → N-(2-hydroxy-5-nitrophenyl)butanamide

HRID 40116

Reaction equation

HRID 40116 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[CH2:12]([C:15](Cl)=[O:16])[CH2:13][CH3:14].N1C=CC=CC=1>C1COCC1.CCOC(C)=O>[OH:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[NH:1][C:15](=[O:16])[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 1049PyridineHCID 8855Butyryl chlorideHCID 36133892-Amino-4-Nitrophenol

Product 1

HCID 3599768N-(2-hydroxy-5-nitrophenyl)butanamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-amino-4-nitrophenol (Aldrich, 1.0 g, 6.5 mmol) in THF (25 ml) was added n-PrCOCl (694 mg, 6.5 mmol) and pyridine (2.6 ml, 32.4 mmol). The reaction was refluxed for 5 days, diluted with EtOAc, washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes) to yield the title compound as a brown solid.

Workup

  1. temperatureThe reaction was refluxed for 5 days
  2. washwashed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-deba7b892d654a9ba33e0d0fda19e694
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Linked notes

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