Water → HCID 13938483, compound

HRID 576075Notes

Reaction equation

HRID 576075 reaction equation
C(=O)([O-])[O-].[K+].[K+].CI.[F:9][C:10]1C=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:11]=1N.O.[CH3:21][N:22]([CH3:25])[CH:23]=O>>[F:9][C:10]1[CH:11]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][C:23]=1[N:22]([CH3:25])[CH3:21]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 677852-Fluoro-5-nitroaniline

Product 1

HCID 13938483HCID 13938483, compound

Conditions

Temperature
100 °C

Procedure

Potassium carbonate (4.15 g, 30 mmol) and methyl iodide (1.49 mL, 24.0 mmol) were added to a solution of 2-fluoro-5-nitroaniline (1.56 g, 10.0 mmol) in N,N-dimethylformamide (30 mL) at room temperature and the mixture was stirred at 100° C. for 6 hr. After cooling to room temperature, water was added to the reaction mixture and the mixture was extracted three times with ethyl acetate. The organic layer was washed with 1 mol/L hydrochloric acid and brine and dried over anhydrous magnesium sulfate and then the desiccant was filtered off, followed by concentration under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to afford 2-fluoro-N,N-dimethyl-5-nitroaniline as a pale yellow oil (290 mg).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted three times with ethyl acetate
  3. washThe organic layer was washed with 1 mol/L hydrochloric acid and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationthe desiccant was filtered off
  6. concentrationfollowed by concentration under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-dc59117beaf94f0a8f58bb2966491bcf
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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