4-Nitroaniline → HCID 2954971, compound

HRID 2079587Notes

Reaction equation

HRID 2079587 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-dimethylimidazoliumhexafluorophosphate and 1.53 mL (111.0 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-d6ec300a224c4fd28bc078ed3941c1f2
Source dataset
uspto-grants-2011_04
Patent number
US07932250B2

Reaction notes

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