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

HRID 2251863ノート

反応式

HRID 2251863 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-88b01dd7eba94d3793815f4642993054
出典データセット
uspto-grants-2008_01
特許番号
US07320992B2

反応ノート

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