4-Cyclopropyl-2-fluoro-1-nitrobenzene → 4-Cyclopropyl-2-fluoroaniline

HRID 79005Notes

Reaction equation

HRID 79005 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[C:6]([F:13])[CH:5]=2)[CH2:3][CH2:2]1>[Pd]>[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([F:13])[CH:5]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 574239144-Cyclopropyl-2-fluoro-1-nitrobenzene

Product 1

HCID 201000714-Cyclopropyl-2-fluoroaniline

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A slurry of palladium on carbon (200 mg, 10% wt.) in IMS was added to a degassed solution of 4-cyclopropyl-2-fluoro-1-nitro-benzene (1.45 g, 8 mmol) in IMS (50 mL), the atmosphere was evacuated and back-filled with nitrogen then re-evacuated and back-filled with hydrogen. The reaction mixture was stirred under 1 atmosphere pressure of hydrogen at room temperature for 24 hours before filtering through a pad of Celite® then washing with ethyl acetate. The filtrate was concentrated in vacuo to give the title compound as a pale purple residue (1.19 g, 98%). 1H NMR (CDCl3, 400 MHz) 6.72-6.63 (3 H, m), 3.56 (2 H, s), 1.83-1.75 (1 H, m), 0.93-0.82 (2 H, m), 0.59-0.54 (2 H, m).

Workup

  1. customthe atmosphere was evacuated
  2. additionback-filled with nitrogen
  3. customthen re-evacuated
  4. additionback-filled with hydrogen
  5. filtrationbefore filtering through a pad of Celite®
  6. washthen washing with ethyl acetate
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2302825d079e47f0adefdbb94b9c8aa3
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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