Dimethylformamide → 2-(2-(4-Fluorophenylamino)ethyl)iso-indoline-1,3-dione

HRID 445376Notes

Reaction equation

HRID 445376 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([N:9]([CH2:12][CH2:13]Br)[C:10](=[O:11])[C:4]2=[CH:3][CH:2]=1)=[O:8].[F:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.CN(C=O)C.C(=O)([O-])[O-].[Na+].[Na+]>O>[F:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][CH2:13][CH2:12][N:9]2[C:7](=[O:8])[C:5]3[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=3)[C:10]2=[O:11])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 97314-FluoroanilineHCID 10340Sodium CarbonateHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-

Product 1

HCID 174039152-(2-(4-Fluorophenylamino)ethyl)iso-indoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a 50 mL round-bottomed flask was added n-(2-bromoethyl)phthalimide, 95% (508 mg, 1999 μmol, Aldrich), 4-fluoroaniline (193 μL, 1999 μmol, Aldrich), DMF (2 mL), sodium carbonate (336 mg, 3999 μmol). The reaction mixture was stirred at 80° C. for overnight. The reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2×40 mL). The organic extract was washed with water (20 mL), saturated NaCl (20 mL), dried over Na2SO4, filtered and concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 30% EtOAc/hexanes to give 2-(2-(4-fluorophenylamino)ethyl)iso-indoline-1,3-dione. MS (ESI pos. ion) m/z: 285 (M+1).

Workup

  1. extractionextracted with EtOAc (2×40 mL)
  2. extractionThe organic extract
  3. washwas washed with water (20 mL), saturated NaCl (20 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customthe residue was purified by silica gel chromatography
  8. washeluting with 30% EtOAc/hexanes

Sources & evidence

ORD record
ord-13f53f6f2b3b4379988a5d94f082704f
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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