Ammonium Chloride → HCID 21106569, Verbindung

HRID 1765355Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1765355
C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12]([Br:16])=[N:11][N:10]([CH:17]([CH3:19])[CH3:18])[C:9]2=[O:20])=O)C.[Li+].[BH4-].[NH4+].[Cl-]>O1CCCC1>[Br:16][C:12]1[C:13]2[C:8](=[CH:7][C:6]([CH2:4][OH:3])=[CH:15][CH:14]=2)[C:9](=[O:20])[N:10]([CH:17]([CH3:19])[CH3:18])[N:11]=1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 4148881Lithium borohydride2×HCID 68898772Bromo-3-isopropyl-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid ethyl ester

Produkt 1

HCID 21106569HCID 21106569, VerbindungAusbeute 44,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Bromo-3-isopropyl-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid ethyl ester (2.3 g, 6.8 mmol) was suspended in tetrahydrofuran (THF) (50 ml) and cooled to 0° C. To the suspension was added LiBH4 (5.1 ml of a 2M solution in THF, 10.2 mmol) dropwise, the suspension was allowed to warm to room temperature and stirred for 24 hours. After this time, LC-MS showed 50% starting material remained. To this was added LiBH4 (1.7 ml of a 2M solution in THF, 3.4 mmol) and the reaction mixture was stirred for a further 3 hours. The reaction was cooled to 0° C., saturated NH4Cl (40 ml) was added and the reaction mixture was then partitioned between water (50 ml) and dichloromethane (DCM) (150 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated under vacuum. The resulting residue was then purified by flash column chromatography (elution: 50% toluene, 30% ethyl acetate, 20% DCM) to give the title compound (0.9 g, 43% yield) as a white solid.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. stirringwas stirred for a further 3 hours
  3. temperatureThe reaction was cooled to 0° C.
  4. customthe reaction mixture was then partitioned between water (50 ml) and dichloromethane (DCM) (150 ml)
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe resulting residue was then purified by flash column chromatography (elution: 50% toluene, 30% ethyl acetate, 20% DCM)

Quellen und Nachweise

ORD-Eintrag
ord-4dced36c0a204e36a4fb24cb4ce14fa9
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07226923B2

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