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Phosphorus oxide (P4O10) → 3,5-Diphenyl-1H-pyrazolo[4,3-c]isoquinoline

HRID 1760164
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1760164
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[C:15]1([C:21]2[C:25]([NH:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:24]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[NH:23][N:22]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.P(Cl)(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>C1(C)C(C)=CC=CC=1>[C:15]1([C:21]2[C:25]3[N:26]=[C:27]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:39]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[C:24]=3[NH:23][N:22]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 14812Phosphorus oxide (P4O10)HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 12094555HCID 12094555, Verbindung

Produkt 1

HCID 100874193,5-Diphenyl-1H-pyrazolo[4,3-c]isoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237
O-Xylene
Lösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

201 mg of phosphorus pentoxide were added to a solution of 240 mg of N-(3,5-diphenyl-1H-pyrazol-4-yl)benzylamine (2) in 10 ml of xylene, after which 195 μl of phosphorus oxychloride were added dropwise at 150° C. The reaction solution was stirred at 150° C. for 4 h and then stirred at RT for 12 h; a saturated solution of sodium hydrogen carbonate was then added and the whole was extracted with methylene chloride. The organic phase was dried over magnesium sulfate, concentrated under reduced pressure and purified by means of HPLC (Merk-Hibar-Lichrospher 100-RP-18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90). The following was obtained: 1. C22H15N3 (321.38); MS (ESI) 322 (M+H)

Aufarbeitung

  1. stirringstirred at RT for 12 h
  2. extractionthe whole was extracted with methylene chloride
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. custompurified by means of HPLC (Merk-Hibar-Lichrospher 100-RP-18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90)
  6. customThe following was obtained

Quellen und Nachweise

ORD-Eintrag
ord-5df9ce1b75f54d6eb26223589d1240f5
Quelldatensatz
uspto-grants-2005_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06841556B2

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