4-Cyclopropyl-1-fluoro-2-nitrobenzene → 5-Cyclopropyl-2-fluoroaniline

HRID 1898323Notes

Reaction equation

HRID 1898323 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([F:10])=[C:6]([N+:11]([O-])=O)[CH:5]=2)[CH2:3][CH2:2]1>C(O)(=O)C.[Fe]>[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([F:10])=[C:6]([CH:5]=2)[NH2:11])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 569685734-Cyclopropyl-1-fluoro-2-nitrobenzene

Product 1

HCID 675036775-Cyclopropyl-2-fluoroanilineYield 77.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 4-cyclopropyl-1-fluoro-2-nitrobenzene (0.700 g, 4.26 mmol) in acetic acid (6.0 mL) was added iron powder (1.0 g). The reaction mass was stirred at RT for 2 h. The reaction mass was quenched in water and basified with NaHCO3, extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 0.500 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 0.50-0.52 (m, 2H), 0.83-0.85 (m, 2H), 1.71-1.74 (m, 1H), 4.97 (s, 2H), 6.21 (m, 1H), 6.44 (d, J=9.0 Hz, 1H), 6.77-6.84 (m, 1H).

Workup

  1. customThe reaction mass was quenched in water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b0d24f65b9944f6b8e8fe20afcc73240
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

Loading…