Pyridine → ST50554379

HRID 722406Notes

Reaction equation

HRID 722406 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH:12]1([C:18](Cl)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.N1C=CC=CC=1.C(OCC)(=O)C>C1COCC1>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:18]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:19])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 677684-Fluoro-3-nitroanilineHCID 75938Cyclohexanecarbonyl chloride

Product 1

HCID 3598338ST50554379Yield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-fluoro-3-nitro aniline (1.41 g, 9.0 mmol) in THF (50 mL) was added cyclohexanecarbonyl chloride (1.46 g, 9.6 mmol) and pyridine (0.97 mL, 12 mmol), and the mixture stirred for 22 h at room temperature. Ethyl acetate (100 mL) was added, and the solution was washed in turn with 1M HCl (50 mL) and saturated sodium bicarbonate (50 mL). The organic layer was dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography, eluting with hexane/ethyl acetate (7:3) to give cyclohexanecarboxylic acid (4-fluoro-3-nitro-phenyl)amide (1.35 g, 56%).

Workup

  1. washthe solution was washed in turn with 1M HCl (50 mL) and saturated sodium bicarbonate (50 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customevaporated
  4. customThe residue was purified by flash chromatography
  5. washeluting with hexane/ethyl acetate (7:3)

Sources & evidence

ORD record
ord-aa97690127194248be6376ee0df97654
Source dataset
uspto-grants-2006_11
Patent number
US07138420B2

Reaction notes

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