Hydrochloric Acid → 5-Amino-4-(2-chlorophenyl)-2-ethylthieno[2,3-b]pyridine

HRID 1885202Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1885202
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13]([N+:14]([O-])=O)=[CH:12][N:11]=[C:10]2[S:17][C:18]([CH2:20][CH3:21])=[CH:19][C:9]=12.Cl.O.O.[Sn](Cl)Cl.[OH-].[Na+]>C(Cl)(Cl)Cl.O.O1CCOCC1>[NH2:14][C:13]1[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[C:9]2[CH:19]=[C:18]([CH2:20][CH3:21])[S:17][C:10]2=[N:11][CH:12]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 197871684-(2-Chlorophenyl)-2-ethyl-5-nitrothieno[2,3-b]pyridine

Produkt 1

HCID 197871805-Amino-4-(2-chlorophenyl)-2-ethylthieno[2,3-b]pyridineAusbeute 85,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a mixture of 4-(2-chlorophenyl)-2-ethyl-5-nitrothieno[2,3-b]pyridine (4.0 g), dioxane (25 ml) and conc. hydrochloric acid (12.5 ml) was added tin(II) chloride dihydrate (8.5 g). After stirring at room temperature for one hour, water was added to the mixture, which was made strong alkaline with 6N NaOH and then extraced with chloroform. The extract was washed with water and dried over MgSO4 and the solvent was distilled off. The residue was chromatographed on a silica gel column and eluted with hexane-ethyl acetate (4 : 1). The solvent was distilled off and to the residue was added hexane to obtain 5-amino-4-(2-chlorophenyl)-2-ethylthieno[2,3-b]pyridine (3.1 g, 85.6%) as crystals. The crystals were recrystallized from isopropyl ether to obtain colorless prisms, mp: 87°-88° C.

Aufarbeitung

  1. washThe extract was washed with water
  2. dry with materialdried over MgSO4
  3. distillationthe solvent was distilled off
  4. customThe residue was chromatographed on a silica gel column
  5. washeluted with hexane-ethyl acetate (4 : 1)
  6. distillationThe solvent was distilled off and to the residue
  7. additionwas added hexane

Quellen und Nachweise

ORD-Eintrag
ord-dc1486e684ed400faeba6e69bfd3aee3
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05143919

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