Dimethylformamide → N-Methyl-4-(4-nitrophenoxy)-2-nitroaniline

HRID 1294059Notes

Reaction equation

HRID 1294059 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:22]=[CH:21][C:9]([O:10][C:11]2[CH:17]=[CH:16][C:14]([NH2:15])=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=2)=[CH:8][CH:7]=1)([O-:5])=[O:4].[CH3:23]N(C=O)C>>[CH3:23][NH:15][C:14]1[CH:16]=[CH:17][C:11]([O:10][C:9]2[CH:21]=[CH:22][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][CH:8]=2)=[CH:12][C:13]=1[N+:18]([O-:20])=[O:19]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 12032722Benzenamine, 2-nitro-4-(4-nitrophenoxy)-2×

Product 1

HCID 17755333N-Methyl-4-(4-nitrophenoxy)-2-nitroaniline

Conditions

Temperature
0 °C

Procedure

To a mixture of NaH (60% oily, 320 mg, 8.0 mmol) in DMF (30 mL) was added a solution of 4-(4-nitrophenoxy)-2-nitroaniline (Intermediate 8A-2.00 g, 7.3 mmol) in DMF (30 mL) at 0° C. followed by an excess amount of Mel (2.0 mL). The mixture was stirred at 0° C. for 1.5 hrs then at room temperature overnight. The mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4 then evaporated. Sequence purification on SiO2column chromatography gave the title compound (2.10 g, quant). ): 1H NMR (CDCl3-d1) δ 3.08 (d, 3H), 6.94 (d, 1H), 7.00 (d, 2H), 7.30 (dd, 1H), 7.97 (d, 1H), 8.08 (brs, 1H), 8.22 (d, 2H).

Workup

  1. customat room temperature
  2. customovernight
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. customthen evaporated
  7. customSequence purification on SiO2column chromatography

Sources & evidence

ORD record
ord-9e94a474f9c74874bdfad9bf6adddf9a
Source dataset
uspto-grants-2007_07
Patent number
US07238813B2

Reaction notes

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