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Hydrochloric Acid → 8-Chloro-2-(2-(quinolin-2-YL)ethyl)phthalazin-1(2H)-one

HRID 920920
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 920920
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[N:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][C:33]=1[CH2:42][CH2:43]O.[Cl:45][C:46]1[CH:47]=[CH:48][CH:49]=[C:50]2[C:55]=1[C:54](=[O:56])[NH:53][N:52]=[CH:51]2.Cl>C1COCC1>[Cl:45][C:46]1[CH:47]=[CH:48][CH:49]=[C:50]2[C:55]=1[C:54](=[O:56])[N:53]([CH2:43][CH2:42][C:33]1[CH:34]=[CH:35][C:36]3[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:32]=1)[N:52]=[CH:51]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 705322-QuinolineethanolHCID 5462977Diethyl azodicarboxylateHCID 713076628-Chloro-1(2H)-phthalazinone

Produkt 1

HCID 717436398-Chloro-2-(2-(quinolin-2-YL)ethyl)phthalazin-1(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of triphenylphosphine (9.00 g, 34.3 mmol) in THF (100 mL), DEAD (5.44 mL, 34.3 mmol) was added at 0° C. After stirring for 15 min, 2-(quinolin-2-yl)ethanol from Example a1 (2.97 g, 17.17 mmol) was added. After another 15 min, 8-chlorophthalazin-1(2H)-one (3.1 g, 17.17 mmol) was added. The mixture was stirred overnight at room temperature; LC-MS indicated complete conversion to the product. 1 N HCl was added (pH=4). The mixture was extracted with EtOAc (3×50 mL), the EtOAc layers were discarded. The aqueous layer was neutralized by aq.NaHCO3 and extracted with ethyl acetate (3×500 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was suspended in EtOAc. The solid was filtered through a Büchner funnel. The purity of the title product was 95%.

Aufarbeitung

  1. waitAfter another 15 min
  2. stirringThe mixture was stirred overnight at room temperature
  3. extractionThe mixture was extracted with EtOAc (3×50 mL)
  4. extractionNaHCO3 and extracted with ethyl acetate (3×500 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. filtrationThe solid was filtered through a Büchner funnel

Quellen und Nachweise

ORD-Eintrag
ord-a7ca25ba64f14cc09726916b3f7c2876
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09273068B2

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