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

HRID 243116Notes

Reaction equation

HRID 243116 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>C(#N)C>[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 6342AcetonitrileSolvent

Procedure

2,4-Difluoro-1-nitrobenzene (2.00 g, 12.57 mmol) was dissolved in acetonitrile (20 mL) and DIPEA (2.2 mL, 12.57 mmol) added, followed by the dropwise addition of benzylamine (1.35 g, 12.57 mmol). The reaction mixture was stirred at RT, under an atmosphere of nitrogen overnight. The mixture was concentrated in vacuo to afford the title compound as a yellow oil, which solidified on standing (3.8 g, 100%). The crude material was used without purification in the next step. 1H NMR (CDCl3, 400 MHz): δ 8.55 (1H, s), 8.25 (1H, dd, J=9.46, 6.08 Hz), 7.43-7.29 (5H, m), 6.47 (1H, dd, J=11.35, 2.60 Hz), 6.39 (1H, ddd, J=9.46, 7.28, 2.61 Hz), 4.51 (2H, d, J=5.60 Hz)

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-5f76aee03702477fb30c2ab0a2fd4c0d
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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