Methylamine → 4-(Methylamino)-3-nitrobenzonitrile

HRID 2121920Notes

Reaction equation

HRID 2121920 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH3:13][NH2:14]>C1COCC1>[CH3:13][NH:14][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 27746544-Fluoro-3-nitrobenzonitrile

Product 1

HCID 46007154-(Methylamino)-3-nitrobenzonitrileYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Fluoro-3-nitrobenzonitrile (0.25 g, 1.5 mmol) was cautiously added to a solution of methylamine (2.0 M, 5.0 mL) in THF. The mixture was stirred at room temperature for 8 h, concentrated under reduced pressure, and chromatographed (silica gel, DCM) to give the title product (0.18 g, 68%) as a yellow solid. 1H-NMR (CDCl3): δ 8.52 (1H, d), 8.41 (1H, br s), 7.64 (1H, dd), 6.92 (1H, d), 3.10 (3H, d).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customchromatographed (silica gel, DCM)

Sources & evidence

ORD record
ord-8e93867ab6444e19a876ccd93e118953
Source dataset
uspto-grants-2004_02
Patent number
US06696473B2

Reaction notes

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