4-Fluoroaniline → HCID 23084565, compound

HRID 2111639Notes

Reaction equation

HRID 2111639 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])/[C:7](=[CH:12]\[C:13]([O:15][CH2:16][CH3:17])=[O:14])/O[C:5]2=[O:18].[F:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1>C(O)(=O)C>[CH3:11][C:10]1[CH:9]=[C:8]2[C:4](=[CH:3][C:2]=1[CH3:1])[C:5](=[O:18])[N:24]([C:23]1[CH:25]=[CH:26][C:20]([F:19])=[CH:21][CH:22]=1)/[C:7]/2=[CH:12]/[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 13056244HCID 13056244, compound

Product 1

HCID 23084565HCID 23084565, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl (E)-5,6-dimethyl-3-oxo-1,3-dihydroisobenzofuran-1-ylideneacetate (0.20 g, 0.81 mmol) and 4-fluoroaniline (0.10 g, 0.89 mmol) were stirred with heating in acetic acid at 110° C. for 7 hrs. The reaction solution was concentrated under reduced pressure, and methanol was added to the residue. The resulting crystals were collected by filtration, and dried to give 0.24 g of 5,6-dimethyl-3-[(E)-2-ethoxy-2-oxoethylidene]-2-(4-fluoro-phenyl)isoindolin-1-one [IUPAC name: ethyl 2-[2-(4-fluorophenyl)-5,6-dimethyl-3-oxo-2,3-dihydro-1H-isoindol-1-ylidene]acetate].

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, and methanol
  2. additionwas added to the residue
  3. filtrationThe resulting crystals were collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-4ccba64285b949b5b5eb5361b43dee09
Source dataset
uspto-grants-2009_04
Patent number
US07521451B2

Reaction notes

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