N-Ethylphthalimide → 2-ethyl-3-hydroxy-1,3-dihydro-2H-isoindol-1-one

HRID 733216

Reaktionsgleichung

Reaktionsgleichung von HRID 733216
[CH2:1]([N:3]1[C:7](=[O:8])[C:6]2=[CH:9][CH:10]=[CH:11][CH:12]=[C:5]2[C:4]1=[O:13])[CH3:2]>CO.[BH4-].[K+]>[OH:8][CH:7]1[C:6]2[C:5](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4](=[O:13])[N:3]1[CH2:1][CH3:2]

Komponenten

4

Edukt 1

HCID 21120N-Ethylphthalimide

Produkt 1

HCID 153059102-ethyl-3-hydroxy-1,3-dihydro-2H-isoindol-1-oneAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 4192641Potassium borohydrideLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

3-Hydroxy-2-ethyl-2,3-dihydroisoindol-1-one is prepared as described in Example 1, starting with 4.0 g of N-ethylphthalimide in 20 cm3 of methanol and 1.2 g of potassium borohydride. The reaction mixture is stirred at a temperature in the region of 20° C. for 20 hours and is then cooled to a temperature in the region of 0° C. and distilled water is added dropwise. The precipitate obtained is filtered off and then washed with cold water. The methanol is then partially evaporated from the filtrate under reduced pressure (2 kPa) at a temperature in the region of 35° C., and the residue is cooled to 0° C. The second precipitate thus obtained is filtered off and then washed with cold water. The two fractions of solid are dried under reduced pressure (2 kPa) at a temperature in the region of 35° C. 1.9 g of 3-hydroxy-2-ethyl-2,3-dihydroisoindol-1-one are thus obtained in the form of a flaky white powder. (Rf=0.5, thin layer chromatography on silica gel, eluent: cyclohexane/ethyl acetate (30/70 by volume)).

Aufarbeitung

  1. custom3-Hydroxy-2-ethyl-2,3-dihydroisoindol-1-one is prepared
  2. temperatureis then cooled to a temperature in the region of 0° C.
  3. distillationdistilled water
  4. additionis added dropwise
  5. customThe precipitate obtained
  6. filtrationis filtered off
  7. washwashed with cold water
  8. customThe methanol is then partially evaporated from the filtrate under reduced pressure (2 kPa) at a temperature in the region of 35° C.
  9. temperaturethe residue is cooled to 0° C
  10. customThe second precipitate thus obtained
  11. filtrationis filtered off
  12. washwashed with cold water
  13. customThe two fractions of solid are dried under reduced pressure (2 kPa) at a temperature in the region of 35° C

Quellen und Nachweise

ORD-Eintrag
ord-7539f4e08ff74215a8cb335e7b8b9f2b
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589117B2

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