Ethyl Acetate → 2-(4-Tert-butyl-phenyl)-3-hydroxy-3-methyl-7-nitro-2,3-dihydro-isoindol-1-one

HRID 2251863Notes

Reaction equation

HRID 2251863 reaction equation
Br[CH2:2][CH:3]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[C:5](=[O:15])[O:4]1.[C:16]([C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17].CCOC(C)=O>C1COCC1.O>[C:16]([C:20]1[CH:21]=[CH:22][C:23]([N:24]2[C:3]([OH:4])([CH3:2])[C:11]3[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=3)[C:5]2=[O:15])=[CH:25][CH:26]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 698614-Tert-ButylanilineHCID 596443873-bromomethyl-7-nitro-3H-isobenzofuran-1-one

Product 1

HCID 690317142-(4-Tert-butyl-phenyl)-3-hydroxy-3-methyl-7-nitro-2,3-dihydro-isoindol-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The mixture of 3-bromomethyl-7-nitro-3H-isobenzofuran-1-one (0.50 g, 1.84 mmol, Step E) and 4-tert-butylaniline (1.20 mL, 7.36 mmol) in 20 mL of THF was slowly warmed to RT from 0° C., then heated to reflux for 24 h. After cooling to RT, the mixture was diluted with H2O, and extracted with EtOAc. The combined organic portions were washed with brine, dried over MgSO4, filtered, condensed, and the titled compound was obtained as a light yellowish solid after column chromatography (10 to 35% of EtOAc in hexanes).

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 h
  3. temperatureAfter cooling to RT
  4. extractionextracted with EtOAc
  5. washThe combined organic portions were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customcondensed

Sources & evidence

ORD record
ord-88b01dd7eba94d3793815f4642993054
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

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