Potassium Carbonate → RS 14203

HRID 861971Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 861971
[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].[H-].[Na+].Cl.[N:24]1[CH:29]=[CH:28][C:27]([CH2:30]Cl)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.C1(C)C=CC=CC=1>[N:24]1[CH:29]=[CH:28][C:27]([CH2:30][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:26][CH:25]=1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 745704-(Chloromethyl)pyridinium chlorideHCID 197007208-(3-Nitrophenyl) pyrido[2,3-d]pyridazin-5-one

Produkt 1

HCID 9808563RS 14203Ausbeute 52,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

8-(3-nitrophenyl)-pyrido[2,3-d]pyridazin-5-one (5.12 g, 19.1 moles), sodium hydride (50% in oil, 1 g, 20.1 moles) were mixed in 100 mL of 1-methyl-2-pyrrolidone and the mixture heated to 65° C. In a separatory funnel, 4-picolyl chloride hydrochloride (4.5 g, 27.4 mmoles), 20 mL of saturated potassium carbonate and 75 mL of toluene are mixed. After separation, the toluene solution was added to the reaction mixture dropwise over the period of 1 hour. The reaction mixture was diluted with water (250 mL) and extracted twice with ethyl acetate (200 mL). After concentrating the organic fractions, methanol and hexanes (75 mL each) were added and the mixture allowed to stir at room temperature for 17 hours. The material was filtered and dried to yield 5.2 g of 6-(4-pyridylmethyl)-8-(3-nitro-phenyl)-pyrido[2,3-d]pyridazin-5-one.

Aufarbeitung

  1. customAfter separation
  2. additionthe toluene solution was added to the reaction mixture dropwise over the period of 1 hour
  3. additionThe reaction mixture was diluted with water (250 mL)
  4. extractionextracted twice with ethyl acetate (200 mL)
  5. concentrationAfter concentrating the organic fractions, methanol and hexanes (75 mL each)
  6. additionwere added
  7. filtrationThe material was filtered
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-790ee26f13044181a6017ad3805f8266
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05716954

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