1-Tert-butyl-2-vinyl-3-nitrobenzene → HCID 22061166, compound

HRID 498921Notes

Reaction equation

HRID 498921 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[C:6]=1[CH:14]=[CH2:15])([CH3:4])([CH3:3])[CH3:2].C(C1C(C=C)=C(N)C=CC=1)(C)(C)C>[Pd].CO>[C:1]([C:5]1[C:6]([CH2:14][CH3:15])=[C:7]([NH2:11])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 684623661-Tert-butyl-2-vinyl-3-nitrobenzeneHCID 684632113-Tert-butyl-2-ethenylaniline

Product 1

HCID 22061166HCID 22061166, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a hydrogenation apparatus, a mixture of 1,5 g (8,55 mmol) 1-tert-butyl-2-vinyl-3-nitrobenzene and 250 mg 5% Pd/C and 20 ml of absolute methanol is hydrogenated at room temperature for 2,5 hours. The catalyst is filtered off and the solvent is evaporated in a water jet vacuum. The crude reaction product can be used directly for further chemical transformations. This gives 1,5 g 3-tert-butyl-2-vinyl-phenylamine in the form of a slightly brownish liquid (98% of theory).

Workup

  1. waitis hydrogenated at room temperature for 2,5 hours
  2. filtrationThe catalyst is filtered off
  3. customthe solvent is evaporated in a water jet vacuum
  4. customThe crude reaction product

Sources & evidence

ORD record
ord-9afa0ed7125f44b9a6fd29e53e214e14
Source dataset
uspto-grants-2010_08
Patent number
US07767625B2

Reaction notes

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