Methyl iodide → 4-Methoxy-N-methyl-2-nitrobenzenamine

HRID 1048987Notes

Reaction equation

HRID 1048987 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.[H-].[Na+].[CH3:15]I>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH3:15])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 667934-Methoxy-2-nitroaniline

Product 1

HCID 35543134-Methoxy-N-methyl-2-nitrobenzenamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-methoxy-2-nitro-phenylamine (5.0 g, 0.029 mol) in DMF (25 ml) was added NaH (0.9 g, 0.035 mol) at 0° C. and stirred at that temperature for 30 min. Methyl iodide (2.17 ml, 0.035 mol) was added and the resulting solution was stirred at room temperature for 30 min. The reaction was quenched with ice-water and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with brine dried over Na2SO4 and concentrated under vacuum to afford the title compound (4-methoxy-2-nitro-phenyl)-methyl-amine as a red solid. C8H10N2O3; 1H NMR (400 MHz, CDCl3), δ: 8.00 (brs, 1H), 7.62 (d, J=2.4 Hz, 1H), 7.18 (dd,1=9.2 Hz, J2=2.0 Hz, 1H), 6.82 (d, J=9.6 Hz, 1H), 3.81 (d, J=14.8 Hz, 3H), 3.02 (s, 3H). MS (M+1): 183.1.

Workup

  1. stirringthe resulting solution was stirred at room temperature for 30 min
  2. customThe reaction was quenched with ice-water
  3. extractionextracted with ethyl acetate (3×100 ml)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6b9c3a64e1ca465fad46e2963325afa1
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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