Water → HCID 13769242, Verbindung

HRID 2232509Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2232509
[H-].[Na+].[C:3]([O:11]CC)(=[O:10])[CH2:4][C:5](OCC)=O.BrC[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[C:18]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:17]=1.O>O1CCCC1>[C:26]1([C:18]2[N:17]=[C:16]([CH2:5][CH2:4][C:3]([OH:11])=[O:10])[C:25]3[C:20]([CH:19]=2)=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 13769241HCID 13769241, Verbindung

Produkt 1

HCID 13769242HCID 13769242, VerbindungAusbeute 44,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Sodium hydride (6.5 g, 80% strength in oil) is placed with tetrahydrofuran (160 cc) under nitrogen, and a solution of diethyl malonate (34.9 g) in anhydrous tetrahydrofuran (200 cc) is added dropwise. After 1 hour's stirring at room temperature (approximately 20° C.), a solution of 1-bromomethyl-3-phenylisoquinoline (16.2 g) in anhydrous tetrahydrofuran (200 cc) is added. After 20 hours' stirring at 20° C., water (200 cc) is added and the aqueous phase extracted with ethyl acetate. The organic phase is dried and evaporated to dryness under reduced pressure. The residual product is chromatographed on silica gel with a cyclohexane/ethyl acetate (8:2 by volume) mixture as eluant. The product (11.5 g) is recovered, taken up in concentrated hydrochloric acid (115 cc) and brought to boiling for 20 hours. Water (200 cc) is added, and the precipitate is filtered off and washed with water and acetone. 3-Phenyl-1-isoquinolinepropanoic acid (6.7 g) m.p. 160° C., is obtained.

Aufarbeitung

  1. stirringAfter 20 hours' stirring at 20° C.
  2. extractionthe aqueous phase extracted with ethyl acetate
  3. customThe organic phase is dried
  4. customevaporated to dryness under reduced pressure
  5. customThe residual product is chromatographed on silica gel with a cyclohexane/ethyl acetate (8:2 by volume) mixture as eluant
  6. customThe product (11.5 g) is recovered
  7. waitto boiling for 20 hours
  8. additionWater (200 cc) is added
  9. filtrationthe precipitate is filtered off
  10. washwashed with water and acetone

Quellen und Nachweise

ORD-Eintrag
ord-e0c25185bbc54c7c99558c61068981df
Quelldatensatz
uspto-grants-1988_11
Patentnummer
US04788199

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