Cyclohexene → Ferrostatin-1

HRID 2068284Notes

Reaction equation

HRID 2068284 reaction equation
[CH:1]1([NH:7][C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][C:9]=2[N+:19]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1CCCCC=1>C(O)C.[Pd]>[NH2:19][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:8]=1[NH:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 5298559Ethyl 4-(cyclohexylamino)-3-nitrobenzoate

Product 1

HCID 4068248Ferrostatin-1Yield 85.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
83 °C

Procedure

In a 250 mL round bottom flask ethyl 4-(cyclohexylamino)-3-nitrobenzoate (3.01 g, 0.0103 mol) was dissolved in ethanol (40 mL) and 1 gram of 5% palladium on carbon (54.62% water) was added. Cyclohexene (7 mL, 0.07 mol) was then added and the reaction heated at 83° C. for 3 hours. The reaction mixture was filtered through celite and the filter cake washed with ethanol. The combined filtrates were concentrated to give 2.3 g title compound as a brownish tan solid.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe filter cake washed with ethanol
  3. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-57c709ded3ca4524978a93b974c3878d
Source dataset
uspto-grants-2012_10
Patent number
US08293923B2

Reaction notes

Loading…