Dimethylformamide → 5-chloro-N-methyl-2-nitroaniline

HRID 1294061Notes

Reaction equation

HRID 1294061 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[H-].[Na+].[CH3:14]N(C=O)C>>[CH3:14][NH:7][C:6]1[CH:8]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 2580415-chloro-N-methyl-2-nitroaniline

Conditions

Temperature
0 °C

Procedure

To a solution of 5-chloro-2-nitroaniline (1.73 g, 10.0 mmol) in DMF (40 mL) was added NaH (60% oily, 880 mg, 22.0 mmol) at 0° C. followed by excess amount of Mel (3.0 mL). The mixture was stirred at 0° C. for 1 hr 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 SiO2 column chromatography gave the title compound (1.86 g, quant): 1H NMR (DMSO-d6) δ 2.95 (d, 3H), 6.69 (dd, 1H), 7.03 (d, 1H), 8.08 (d, 1H), 8.28 (br, 1H).

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 SiO2 column chromatography

Sources & evidence

ORD record
ord-eb6994968c5d48b9b03b12f48b78b0b2
Source dataset
uspto-grants-2007_07
Patent number
US07238813B2

Reaction notes

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