Sodium Chloride → 7-Hydroxy-2,3-dimethyl-2,3-dihydro-isoindol-1-one

HRID 81345노트

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HRID 81345 반응식
N[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[CH:7]2[CH3:13].N([O-])=[O:15].[Na+].[Na+].[Cl-]>OS(O)(=O)=O>[OH:15][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[CH:7]2[CH3:13]

참가 물질

5

반응물 3

HCID 5234Sodium ChlorideHCID 23668193Sodium NitriteHCID 585226217-Amino-2,3-dimethyl-2,3-dihydro-isoindol-1-one

생성물 1

HCID 585226427-Hydroxy-2,3-dimethyl-2,3-dihydro-isoindol-1-one

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

반응 조건

온도
-10 °C

실험 절차

7-amino-2,3-dimethyl-2,3-dihydro-isoindol-1-one (11.45 g) is suspended in a mixture of ice (27 g) and H2SO4 conc. (9.70 mL) and cooled to −10° C. Aqueous sodium nitrite solution (2.5 molar, 31.18 mL) is added dropwise, so that the temperature does not rise above 0° C. and the solution is stirred for 15 min at this temperature. Then H20 (135 mL) is added and the solution is heated to 80° C. for 15 min. For working up it is combined with 10% NaCl solution (100 mL) and extracted twice with 100 mL of CH2Cl2. The organic phase is extracted with NaOH solution (0.2 molar) and then the aqueous phase is acidified (HCl aq. conc.) and re-extracted with CH2Cl2. The organic phase is dried on magnesium sulphate, filtered off from the desiccant and the solvent is eliminated in vacuo.

후처리

  1. customdoes not rise above 0° C.
  2. additionThen H20 (135 mL) is added
  3. temperaturethe solution is heated to 80° C. for 15 min
  4. extractionextracted twice with 100 mL of CH2Cl2
  5. extractionThe organic phase is extracted with NaOH solution (0.2 molar)
  6. extractionre-extracted with CH2Cl2
  7. customThe organic phase is dried on magnesium sulphate
  8. filtrationfiltered off from the desiccant and the solvent

출처 및 근거

ORD 기록
ord-eb66decfd7a04dac9da722a737a8a581
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846689B2

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