Potassium Iodide → RS 14203

HRID 861954Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 861954
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:15]3[N:16]=[CH:17][CH:18]=[CH:19][C:14]=3[C:13](=[O:20])[NH:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[N:29]1[CH:34]=[CH:33][C:32]([CH2:35]Cl)=[CH:31][CH:30]=1>O1CCCC1>[N:29]1[CH:34]=[CH:33][C:32]([CH2:35][N:12]2[C:13](=[O:20])[C:14]3[CH:19]=[CH:18][CH:17]=[N:16][C:15]=3[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)=[N:11]2)=[CH:31][CH:30]=1

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 745714-(Chloromethyl)pyridineHCID 197007208-(3-Nitrophenyl) pyrido[2,3-d]pyridazin-5-one

Produkt 1

HCID 9808563RS 14203Ausbeute 26,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 8-(3-nitrophenyl)-pyrido[2,3-d]pyridazin-5-one (0.16 g, 0.6 moles) in tetrahydrofuran (50 ml) was added potassium carbonate (0.19 g, 7.1 moles), potassium iodide (1.0 g, 6.0 moles) and 4-picolyl chloride (0.98 g, 6.0 mmoles). The mixture was stirred and refluxed under an inert atmosphere for 18 hours. The solvent was removed under vacuum. The residue was partitioned in methanol/ethyl acetate (1:1), chromatographed in 100% hexane followed by 100% ethyl acetate. The remaining solvent was removed yielding 0.58 g of crude 6-(4-pyridylmethyl)-8-(3-nitrophenyl)pyrido[2,3-d]pyridazin-5-one, which was recrystallized from methanol yielding 0.08 g of the pure compound (37.1%), mp. 167°-168° C.

Aufarbeitung

  1. temperaturerefluxed under an inert atmosphere for 18 hours
  2. customThe solvent was removed under vacuum
  3. customThe residue was partitioned in methanol/ethyl acetate (1:1)
  4. customchromatographed in 100% hexane
  5. customThe remaining solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-19a752b1b84f440dbad589e4b7fefe06
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05716954

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