Methane → Jtc-801

HRID 1070471

Reaktionsgleichung

Reaktionsgleichung von HRID 1070471
[C:1](Cl)(=[O:5])[C:2]([Cl:4])=O.[NH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([NH2:18])[CH:16]=2)[N:11]=[C:10]([CH3:19])[CH:9]=1.[C:20](=[O:23])([O-])O.[Na+].[CH4:25].[CH2:26](O)[CH3:27]>N1C=CC=CC=1>[ClH:4].[NH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([NH:18][C:20](=[O:23])[C:25]3[CH:16]=[CH:17][CH:8]=[CH:9][C:10]=3[CH2:19][O:5][C:1]3[CH:2]=[CH:15][C:14]([CH2:26][CH3:27])=[CH:13][CH:12]=3)[CH:16]=2)[N:11]=[C:10]([CH3:19])[CH:9]=1

Komponenten

7

Edukt 5

HCID 297MethaneHCID 702EthanolHCID 65578Oxalyl chlorideHCID 2239952-Methylquinoline-4,6-diamineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 5311339Jtc-801Ausbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of 2-[(4-ethylphenoxy)methyl]benzoic acid (1.13 g, 4.4 mmol) obtained in Preparation Example 2-1 in chloroform (20 ml) was added oxalyl chloride (0.6 ml, 6.8 mmol) and the mixture was stirred at room temperature for 1 hr. Then the reaction mixture was concentrated under reduced pressure. To the obtained acid chloride were added pyridine (20 ml) and 4,6-diamino-2-methylquinoline (623 mg, 4 mmol) obtained in Preparation Example 1-1 and the mixture was stirred at room temperature for 10 hr. To the reaction mixture was added an aqueous sodium hydrogencarbonate solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over sodium sulfate, and the solvent was evaporated. The obtained crude product was dissolved in ethanol and treated with active charcoal, and the solvent was evaporated. The obtained residue was dissolved in ethyl acetate and 1N hydrochloric acid—ether solution was added. The resulting precipitate was collected by filtration. The obtained solid was heated and dried under reduced pressure to give the title compound (1.06 g, 59%, pale-yellow crystals).

Aufarbeitung

  1. concentrationThen the reaction mixture was concentrated under reduced pressure
  2. customobtained in Preparation Example 1-1
  3. stirringthe mixture was stirred at room temperature for 10 hr
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was evaporated
  8. customThe obtained crude product
  9. customthe solvent was evaporated
  10. dissolutionThe obtained residue was dissolved in ethyl acetate
  11. addition1N hydrochloric acid—ether solution was added
  12. filtrationThe resulting precipitate was collected by filtration
  13. temperatureThe obtained solid was heated
  14. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b0cfc6de62284c53ac99652a5ad5619f
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903094B2

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