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

HRID 2251863노트

반응식

HRID 2251863 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-88b01dd7eba94d3793815f4642993054
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07320992B2

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