P-Anisidine → HCID 68663378, compound

HRID 452609Notes

Reaction equation

HRID 452609 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:5]([O:7][CH3:8])=[O:6].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=1>CS(C)=O.C(OCC)(=O)C>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=2[N+:12]([O-:14])=[O:13])[C:5]([O:7][CH3:8])=[O:6])=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 7732P-AnisidineHCID 592761Methyl 3-fluoro-4-nitrobenzoate

Product 1

HCID 68663378HCID 68663378, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 3-fluoro-4-nitrobenzoate (10.0 g, 54.0 mmol) and p-anisidine (13.3 g, 108 mmol) in dimethylsulfoxide (300 mL) was stirred at 70° C. for 3.5 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from hexane/tetrahydrofuran to give the title compound (12.9 g, yield 79%) as red crystals.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was recrystallized from hexane/tetrahydrofuran

Sources & evidence

ORD record
ord-86bd2bf39a394c198cb25ad7216f292e
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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