Diisopropylethylamine → 4-(2,4-Dimethoxybenzylamino)-3-nitrobenzonitrile

HRID 605854Notes

Reaction equation

HRID 605854 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].CCN(C(C)C)C(C)C.[CH3:22][O:23][C:24]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:25]=1[CH2:26][NH2:27]>C1COCC1>[CH3:22][O:23][C:24]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:25]=1[CH2:26][NH:27][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

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5972502,4-DimethoxybenzylamineHCID 27746544-Fluoro-3-nitrobenzonitrile

Product 1

HCID 669708084-(2,4-Dimethoxybenzylamino)-3-nitrobenzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-fluoro-3-nitrobenzonitrile (5.0 g) in THF (100 mL) was treated with DIEA (6.3 mL) and 2,4-dimethoxybenzylamine (5.0 mL), and then stirred for 24 h. The solvent was evaporated and the crude mixture was dissolved in EtOAc (100 mL). The solution was washed once with 1 M HCl and twice with saturated aqueous NaCl (100 mL each). The organic layer was separated, dried over Na2SO4, filtered, and concentrated in vacuo. Column chromatography (20% EtOAc in DCM) provided 9.25 g of the title compound.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe crude mixture was dissolved in EtOAc (100 mL)
  3. washThe solution was washed once with 1 M HCl and twice with saturated aqueous NaCl (100 mL each)
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7abf7ab4db9342409b14a468854cb43a
Source dataset
uspto-grants-2011_03
Patent number
US07915268B2

Reaction notes

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