N-Cyclopropyl-5-fluoro-2-nitroaniline → 1-N-cyclopropyl-5-fluorobenzene-1,2-diamine

HRID 242951Notes

Reaction equation

HRID 242951 reaction equation
[CH:1]1([NH:4][C:5]2[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=2[N+:12]([O-])=O)[CH2:3][CH2:2]1>CCOC(C)=O.[Pd]>[CH:1]1([NH:4][C:5]2[C:6]([NH2:12])=[CH:7][CH:8]=[C:9]([F:11])[CH:10]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 53621866N-Cyclopropyl-5-fluoro-2-nitroaniline

Product 1

HCID 545925541-N-cyclopropyl-5-fluorobenzene-1,2-diamineYield 105.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of cyclopropyl-(5-fluoro-2-nitrophenyl)amine (6.3 mmol) in EtOAc (60 mL) was added 10% Pd/C (150 mg) and the reaction mixture was stirred at RT under a hydrogen atmosphere for 5 h. The suspension was filtered through a pad of Celite® and the filtrate concentrated in vacuo to afford the title compound as a brown oil (1.1 g, quantitative). 1H NMR (CDCl3, 300 MHz): δ 6.76 (1H, dd, J=10.85, 2.76 Hz), 6.60 (1H, dd, J=8.38, 5.56 Hz), 6.34 (1H, td, J=8.45, 2.82 Hz), 4.15 (1H, br s), 3.03 (2H, br s), 2.45-2.36 (1H, m), 0.80-0.72 (2H, m), 0.56-0.49 (2H, m).

Workup

  1. filtrationThe suspension was filtered through a pad of Celite®
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-7a4864627aa440989ecc6c7685519e5e
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…