4-Amino-m-cresol → 6-Butyryl-7-(4-hydroxy-2-methylphenylamino)-3-methoxythieno[3,2-b]pyridine

HRID 2107629

Reaktionsgleichung

Reaktionsgleichung von HRID 2107629
[C:1]([C:6]1[C:7](Cl)=[C:8]2[S:14][CH:13]=[C:12]([O:15][CH3:16])[C:9]2=[N:10][CH:11]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].[OH:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[C:21]([CH3:26])[CH:20]=1>C1(OC)C=CC=CC=1>[C:1]([C:6]1[C:7]([NH:23][C:22]2[CH:24]=[CH:25][C:19]([OH:18])=[CH:20][C:21]=2[CH3:26])=[C:8]2[S:14][CH:13]=[C:12]([O:15][CH3:16])[C:9]2=[N:10][CH:11]=1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Komponenten

4

Edukt 2

HCID 178194-Amino-m-cresolHCID 230461496-Butyryl-7-chloro-3-methoxythieno[3,2-b]pyridine

Produkt 1

HCID 230461516-Butyryl-7-(4-hydroxy-2-methylphenylamino)-3-methoxythieno[3,2-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7519AnisoleLösungsmittel

Versuchsvorschrift

6-Butyryl-7-chloro-3-methoxythieno[3,2-b]pyridine (1.5 g, 0.0056 mol) and 4-hydroxy-2-methylaniline (1.37 g, 0.011 mol) in anisole (30 ml) were heated under reflux in a nitrogen atmosphere for 36 hours. The solvent was evaporated under reduced pressure and the residue was partitioned between chloroform and sodium bicarbonate solution. The insoluble material was filtered off. The chloroform layer was washed with sodium bicarbonate solution (2×100 ml), dried over magnesium sulphate, filtered and evaporated to give a brown solid. The product was purified by flash chromatography using chloroform as eluant. The solid obtained was recrystallised from ethanol to give the title compound, 0.81 g, m.p. 255°-257°.

Aufarbeitung

  1. temperatureunder reflux in a nitrogen atmosphere for 36 hours
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was partitioned between chloroform and sodium bicarbonate solution
  4. filtrationThe insoluble material was filtered off
  5. washThe chloroform layer was washed with sodium bicarbonate solution (2×100 ml)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customto give a brown solid
  10. customThe product was purified by flash chromatography
  11. customThe solid obtained
  12. customwas recrystallised from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-fed3c7e5755a45e6b84c6a56ff579aae
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04935431

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