2,4-Difluoronitrobenzene → N-Cyclopropyl-5-fluoro-2-nitroaniline

HRID 242950Notes

Reaction equation

HRID 242950 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH:12]1([NH2:15])[CH2:14][CH2:13]1.CCN(C(C)C)C(C)C>CC#N>[CH:12]1([NH:15][C:2]2[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 679672,4-DifluoronitrobenzeneHCID 69828CyclopropylamineHCID 81531Diisopropylethylamine

Product 1

HCID 53621866N-Cyclopropyl-5-fluoro-2-nitroanilineYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2,4-difluoro-1-nitrobenzene (0.7 mL, 6.3 mmol) in anhydrous CH3CN (10 mL) were added cyclopropylamine (0.4 mL, 6.3 mmol) and DIPEA (1.1 mL, 6.3 mmol). The reaction mixture was stirred at RT for 18 h then evaporated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% EtOAc in cyclohexane) to afford the title compound as a yellow solid (6.3 mmol, quantitative). 1H NMR (CDCl3, 300 MHz): δ 8.26-8.09 (2H, m), 6.95 (1H, dd, J=11.43, 2.68 Hz), 6.46-6.35 (1H, m), 2.60-2.50 (1H, m), 0.98-0.89 (2H, m), 0.71-0.63 (2H, m).

Workup

  1. customthen evaporated in vacuo
  2. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-ef91161fa83f483bb0dabe923cf10737
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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