3-Nitroaniline → (3-Fluoro-2-nitro-phenyl)-(3-nitro-phenyl)-amine

HRID 422015Notes

Reaction equation

HRID 422015 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH2:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16](F)[C:15]=1[N+:21]([O-:23])=[O:22].[NH4+].[Cl-]>CN(C=O)C>[F:13][C:14]1[C:15]([N+:21]([O-:23])=[O:22])=[C:16]([NH:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 74233-NitroanilineHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 879221,3-Difluoro-2-nitrobenzene

Product 1

HCID 59804315(3-Fluoro-2-nitro-phenyl)-(3-nitro-phenyl)-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3-nitro-phenylamine (1.82 g, 0.013 mol) in DMF (8 ml) at 0° C. is added NaH (60% dispersion in mineral oil, 0.53 g, 0.013 mol). The reaction is stirred at this temperature for 15 min. Subsequently, a solution of 1,3-difluoro-2-nitro-benzene (0.70 g, 4.4 mmol) in DMF (2 ml) is added slowly. After stirring for additional 30 min, it is poured into a saturated aqueous solution of NH4Cl. The precipitate therefore formed is collected by vacuum filtration. The desired compound is obtained after flash column chromatography purification of the precipitate (silica gel, eluted by hexanes-ethyl acetate). 1H NMR (CDCl3) δ 6.77 (dd, 1H, J=10 Hz, J2=10.6 Hz), 7.11 (d, 1H, J=8.8 Hz), 7.35-7.41 (m, 1H), 7.49-7.59 (m, 2H), 7.99 (dt, 1H, J1=8.0 Hz, J2-2.0 Hz), 8.09 (t, 1H, J=2.0 Hz), 8.35 (bs, 1H); LC-MS: 278.0 (MH+).

Workup

  1. stirringAfter stirring for additional 30 min
  2. customThe precipitate therefore formed
  3. filtrationis collected by vacuum filtration

Sources & evidence

ORD record
ord-f1e4ef325d3641d7b25ba9419b0682c5
Source dataset
uspto-grants-2012_01
Patent number
US08101608B2

Reaction notes

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