Tert-butyl 2-(4-nitrophenyl)ethyl hydrazine-1,2-dicarboxylate → 2-(4-Aminophenyl)ethyl tert-butyl hydrazine-1,2-dicarboxylate

HRID 1892490Notes

Reaction equation

HRID 1892490 reaction equation
[NH:1]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[NH:2][C:3]([O:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1)=[O:4]>C(OCC)(=O)C.[C].[Pd]>[NH:2]([C:3]([O:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)=[O:4])[NH:1][C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18]

Participants

4

Reactant 1

HCID 58112038Tert-butyl 2-(4-nitrophenyl)ethyl hydrazine-1,2-dicarboxylate

Product 1

HCID 581121152-(4-Aminophenyl)ethyl tert-butyl hydrazine-1,2-dicarboxylateYield 58.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 2-(4-nitrophenyl)ethyl hydrazine-1,2-dicarboxylate (9.780 g, 30.00 mmol) in ethyl acetate (100 ml) was added 10% palladium carbon (980.0 mg, containing 50% water), and the mixture was hydrogenated at room temperature and atmospheric pressure. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was suspended in a mixture of hexane (70 ml) and ethyl acetate (30 ml), filtered and dried under reduced pressure to give 2-(4-aminophenyl)ethyl tert-butyl hydrazine-1,2-dicarboxylate (5.207 g, 17.63 mmol, yield 58.8%) as a white solid.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionThe residue was suspended in a mixture of hexane (70 ml) and ethyl acetate (30 ml)
  5. filtrationfiltered
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-404bf1e92644450bbe8598b1fca06a44
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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