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

HRID 81345ノート

反応式

HRID 81345 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

反応条件

温度
-10 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-eb66decfd7a04dac9da722a737a8a581
出典データセット
uspto-grants-2014_09
特許番号
US08846689B2

反応ノート

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