Ammonia → 5-(1-Methylimidazo[4,5-c]pyrid-2-yl)pentanol

HRID 1199994Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1199994
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][CH3:9].C[O:11][CH:12](OC)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]O.C(O)C.N>O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.O>[CH3:9][N:8]1[C:7]2[CH:6]=[CH:5][N:4]=[CH:3][C:2]=2[N:1]=[C:17]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][OH:11]

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 702EthanolHCID 9104124-N-methylpyridine-3,4-diamineHCID 110737396,6-Dimethoxyhexan-1-ol

Produkt 1

HCID 198645195-(1-Methylimidazo[4,5-c]pyrid-2-yl)pentanolAusbeute 30,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 165397Cupric acetate monohydrateKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

3-Amino-4-(methylamino) pyridine (1.23 g), 6,6-dimethoxyhexanol (1.62 g), copper (II) acetate monohydrate (4 g), ethanol (30 ml) and water (30 ml) were mixed and then heated at 150° in a sealed tube for 3 hours. To the cold reaction mixture was added concentrated aqueous ammonia (5 cm3) and the mixture was then filtered through "Hyflo" (Trade Mark), diluted with water (50 ml) and extracted with methylene chloride (3×200 ml). The combined organic extracts were dried over Na2SO4, filtered, and evaporated under vacuum. The residue was chromatographed on silica eluting with a mixture of methylene chloride and methanol. The fractions containing the product were evaporated to leave the title compound, (0.66 g).

Aufarbeitung

  1. temperatureheated at 150° in a sealed tube for 3 hours
  2. customTo the cold reaction mixture
  3. filtrationthe mixture was then filtered through "Hyflo" (Trade Mark)
  4. additiondiluted with water (50 ml)
  5. extractionextracted with methylene chloride (3×200 ml)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated under vacuum
  9. customThe residue was chromatographed on silica eluting with a mixture of methylene chloride and methanol
  10. additionThe fractions containing the product
  11. customwere evaporated

Quellen und Nachweise

ORD-Eintrag
ord-41608628a38546a489eae1f44682f6c2
Quelldatensatz
uspto-grants-1990_02
Patentnummer
US04904671

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