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Phosphorus pentabromide → 1-Bromo-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid

HRID 1783720
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1783720
O=[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[CH:9][CH:10]=2)[C:5](=[O:15])[NH:4][NH:3]1.P(Br)(Br)(Br)(Br)[Br:17]>ClCCCl.CC(O)=O>[Br:17][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[CH:9][CH:10]=2)[C:5](=[O:15])[NH:4][N:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 62678Phosphorus pentabromideHCID 3090561,4-Dioxo-1,2,3,4-tetrahydrophthalazine-6-carboxylic acid

Produkt 1

HCID 211065111-Bromo-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acidAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

1,4-Dioxo-1,2,3,4-tetrahydro-phthalazine-6-carboxylic acid (91.0 g, 0.44 mol) was suspended in DCE (1.0 L) and phosphorus pentabromide (761.0 g, 1.77 mol) was added in three portions and the reaction heated to reflux for 24 hours. The reaction was cooled to RT and poured onto ice (2.5 kg) and the resulting precipitate filtered and washed with water to give the crude product (130.0 g). This crude material was suspended in HOAc (1.6 L) and heated to 125° C. for 2 h. The reaction was cooled to RT and poured onto ice (1.5 kg) and the resulting precipitate filtered. The solid was washed with water and dried to give the title compound (85 g, 73% yield) as a yellow solid. Tr=0.94 min, m/z (ES+) (M+H)+ 310 & 312

Aufarbeitung

  1. temperaturethe reaction heated
  2. temperatureto reflux for 24 hours
  3. additionpoured onto ice (2.5 kg)
  4. filtrationthe resulting precipitate filtered
  5. washwashed with water
  6. customto give the crude product (130.0 g)
  7. temperatureheated to 125° C. for 2 h
  8. temperatureThe reaction was cooled to RT
  9. additionpoured onto ice (1.5 kg)
  10. filtrationthe resulting precipitate filtered
  11. washThe solid was washed with water
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-838951553ef546c1973ea38e16219174
Quelldatensatz
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07501410B2

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