Potassium Carbonate → (2-Methoxy-benzyl)-(2-nitro-phenyl)-amine

HRID 1372838Notes

Reaction equation

HRID 1372838 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH3:11][O:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][NH2:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:11][O:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][NH:16][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 812922-Methoxybenzylamine

Product 1

HCID 7410675(2-Methoxy-benzyl)-(2-nitro-phenyl)-amineYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

25 g (0.177 mole) of 1-Flouro-2-nitrobenzene is added to a 500 ml round bottom flask containing a solution of 200 ml of anhydrous DMF and 24.28 g (0.177 mole) of 2-Methoxybenzylamine. 73.27 g (0.531 mole) of K2CO3 is added and the reaction mixture is stirred at room temperature for 3 hours. The reaction mixture is filtered through celite and washed with 400 ml of ethyl acetate. The filtrate is then washed twice with 200 mL saturated brine and twice with 200 mL water. The organic layer is dried over anhydrous Na2SO4 concentrated in vacuo to afford 32 g (0.13 mole, 76%) of (2-methoxy-benzyl)-(2-nitro-phenyl)-amine (1). 1H NMR (400 MHz, DMSO) 8.6 (m, 1H), 8.0 (m, 1H), 7.4 (m, 1H), 7.2 (m, 2H), 7.0 (m, 1H), 6.8 (m, 2H), 6.6 (m, 1H) 4.6 (m, 2H), 3.8(s, 2H).

Workup

  1. filtrationThe reaction mixture is filtered through celite
  2. washwashed with 400 ml of ethyl acetate
  3. washThe filtrate is then washed twice with 200 mL saturated brine and twice with 200 mL water
  4. dry with materialThe organic layer is dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b04d315577e54385b4ad6286b5b63e0e
Source dataset
uspto-grants-2007_01
Patent number
US07160879B2

Reaction notes

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