4-Nitroaniline → HCID 2954971, compound

HRID 1398071Notes

Reaction equation

HRID 1398071 reaction equation
[CH3:1][O:2][CH2:3][C:4]([OH:6])=O.[N+:7]([C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1)([O-:9])=[O:8].F[P-](F)(F)(F)(F)F.ClC1N(C)C=C[N+]=1C.C(N(CC)CC)C>ClCCl>[CH3:1][O:2][CH2:3][C:4]([NH:14][C:13]1[CH:15]=[CH:16][C:10]([N+:7]([O-:9])=[O:8])=[CH:11][CH:12]=1)=[O:6]

Participants

6

Reactant 4

HCID 74754-NitroanilineHCID 8471TriethylamineHCID 12251Methoxyacetic AcidHCID 11065717HCID 11065717, compound

Product 1

HCID 2954971HCID 2954971, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture solution of 384 μL (5.0 mmol) of methoxyacetic acid and 691 mg (5.0 mmol) of p-nitroaniline in 10 mL of dichloromethane were added 1.53 mg (5.5 mmol) of 2-chloro-1,3-dimethyl imidazolium hexafluorophosphate and 1.53 mL (11.0 mmol) of triethylamine, and the mixture was refluxed for 7 hours. Then, the reaction mixture was extracted with ethyl acetate, the extract was washed with water and saturated saline solution, then, dried over with anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=2/1) to give 750 mg (71%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed for 7 hours
  2. extractionThen, the reaction mixture was extracted with ethyl acetate
  3. washthe extract was washed with water and saturated saline solution
  4. dry with materialdried over with anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-348c24ace7e44ba4833885c672939211
Source dataset
uspto-grants-2014_12
Patent number
US08901315B2

Reaction notes

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