Benzylamine → N-Benzyl-5-fluoro-2-nitroaniline

HRID 930537Notes

Reaction equation

HRID 930537 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].CCN(C(C)C)C(C)C.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCOCC1>[CH2:21]([NH:28][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 679672,4-DifluoronitrobenzeneHCID 81531Diisopropylethylamine

Product 1

HCID 14751679N-Benzyl-5-fluoro-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

2,4-Difluoronitrobenzene E-1.1′″ (3.448 ml; 31.429 mmol) is dissolved in dioxane (35.000 ml). DIPEA (6.601 ml; 40.857 mmol) and benzylamine (3.429 ml; 31.429 mmol) are added. The reaction mixture is stirred at 50° C. overnight. The reaction mixture is concentrated under reduced pressure. The residue crystallises after some minutes. It is triturated with diethyl ether to give the pure crystalline compound.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customThe residue crystallises after some minutes
  3. customIt is triturated with diethyl ether
  4. customto give the pure crystalline compound

Sources & evidence

ORD record
ord-66cb1592d4fe47598cd42c25da41aa5d
Source dataset
uspto-grants-2016_03
Patent number
US09296748B2

Reaction notes

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