Ethanol → 2-[(Z)-C-(3-bromophenyl)-N-(tert-butylamino)carbonimidoyl]pyridin-3-ol

HRID 442733Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 442733
[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[C:5]([C:7]1[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][N:8]=1)=O.Cl.[C:18]([NH:22][NH2:23])([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C.C(O)C>O>[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)/[C:5](/[C:7]1[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][N:8]=1)=[N:23]/[NH:22][C:18]([CH3:21])([CH3:20])[CH3:19]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 8471TriethylamineHCID 81889tert-Butylhydrazine monohydrochlorideHCID 110331762-(3-Bromobenzoyl)-3-hydroxypyridine

Produkt 1

HCID 1364448522-[(Z)-C-(3-bromophenyl)-N-(tert-butylamino)carbonimidoyl]pyridin-3-olAusbeute 24,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 2-(3-bromobenzoyl)-3-hydroxypyridine (0.79 g), t-butylhydrazine hydrochloride (0.53 g), triethylamine (1.2 mL) and ethanol (13 mL) was refluxed for 5 hours. The reaction mixture was poured into water, and subjected to extraction with ethyl acetate. The extract was washed with water and a saturated aqueous saline solution, successively, and dried (sodium sulfate), followed by evaporating the solvent under reduced pressure. The residue was purified by means of a silica gel column (ethyl acetate--hexane) to afford (E)-2-(3-bromo-α-t-butylhydrazinobenzyl)-3-hydroxypyridine (0.60 g) and (Z)-2-(3-bromo-α-t-butylhydrazonobenzyl)-3-hydroxypyridine (0.24 g) (compounds 27 and 26).

Aufarbeitung

  1. temperaturewas refluxed for 5 hours
  2. extractionsubjected to extraction with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materiala saturated aqueous saline solution, successively, and dried (sodium sulfate)
  5. customby evaporating the solvent under reduced pressure
  6. customThe residue was purified by means of a silica gel column (ethyl acetate--hexane)

Quellen und Nachweise

ORD-Eintrag
ord-2a6d8d69912b45f98cfc07f8d08e9f3f
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891895

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