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Sodium Carbonate → 1-Chloro-4-phenyl-5,6,7,8-tetrahydrophthalazine

HRID 911117
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 911117
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:10][C:11]1[C:20]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=2[C:14](Cl)=[N:13][N:12]=1.O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+]>CCOC(C)=O.O.[Cl-].[Na+].O.ClCCl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:10][C:11]1[C:1]2[CH2:6][CH2:5][CH2:4][CH2:3][C:2]=2[C:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[N:13][N:12]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 66827Phenylboronic AcidHCID 126224401,4-Dichloro-5,6,7,8-tetrahydrophthalazine

Produkt 1

HCID 577562221-Chloro-4-phenyl-5,6,7,8-tetrahydrophthalazine

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator
HCID 962WaterLösungsmittel
HCID 6344DichloromethaneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel
HCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (0.270 g, 0.369 mmol), phenylboronic acid (0.900 g, 7.38 mmol) and 1,4-dichloro-5,6,7,8-tetrahydrophthalazine (2.25 g, 11.1 mmol) were combined in a 150 mL sealable vessel under argon. 15 mL dioxane and 2.0 M Sodium carbonate, aqueous (7.38 ml, 14.8 mmol) were added. The vessel was sealed and heated to 80° C. to give a homogenous brown reaction. After 30 min, the reaction was cooled to ambient temperature and was diluted with EtOAc, water, and brine. The layers were separated, and the organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give a red solid. This was taken up in dichloromethane and purified by silica gel chromatography (0-60% EtOAc in hexanes) to give 1-chloro-4-phenyl-5,6,7,8-tetrahydrophthalazine as an off-white solid. MS m/z=245 [M+H]+. Calc'd for C14H13ClN2: 244.7.

Aufarbeitung

  1. customThe vessel was sealed
  2. customto give
  3. customa homogenous brown reaction
  4. temperaturethe reaction was cooled to ambient temperature
  5. customThe layers were separated
  6. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a red solid
  10. custompurified by silica gel chromatography (0-60% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e449e363dee84ebb8055eaa59dcf92b7
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08022221B2

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