Ethyl 4-(cyclohexylamino)-3-nitrobenzoate → Ferrostatin-1

HRID 1788405Notes

Reaction equation

HRID 1788405 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[C:7]([N+:18]([O-])=O)[CH:6]=1)[CH3:2]>C(OCC)(=O)C.CO.[Pd]>[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)=[C:7]([NH2:18])[CH:6]=1)[CH3:2]

Participants

5

Reactant 1

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

Product 1

HCID 4068248Ferrostatin-1

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5.84 g (20 mmol) of Compound 10 in 50 mL ethyl acetate and 30 mL methanol, 100 mg of 10% Pd/C was added, and the mixture was hydrogenated at 30 psi for 6 h. The catalyst was removed by filtration through a pad of Celite, the solvent was evaporated to dryness resulting in a dark purple solid which was recrystallized from ether-hexane. The mother liquid was evaporated, and the resulting solid was suspended in hexane and filtered to give additional yield of Compound 11

Workup

  1. customThe catalyst was removed by filtration through a pad of Celite
  2. customthe solvent was evaporated to dryness
  3. customresulting in a dark purple solid which
  4. customwas recrystallized from ether-hexane
  5. customThe mother liquid was evaporated
  6. filtrationfiltered

Sources & evidence

ORD record
ord-29174407198c49d7a92d8befd421f1d3
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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