N-bromobutanimide → 5-Bromo-6-ethylpyridin-2-amine

HRID 2278894Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2278894
[CH2:1]([C:3]1[N:8]=[C:7]([NH2:9])[CH:6]=[CH:5][CH:4]=1)[CH3:2].C1C(=O)N([Br:17])C(=O)C1>C(Cl)(Cl)Cl>[Br:17][C:4]1[CH:5]=[CH:6][C:7]([NH2:9])=[N:8][C:3]=1[CH2:1][CH3:2]

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 890216-Ethylpyridin-2-amine

Produkt 1

HCID 217103385-Bromo-6-ethylpyridin-2-amineAusbeute 68,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A 0° C. solution of 6-ethylpyridin-2-amine (3.37 g, 27.6 mmol) in CHCl3 (30 mL) was treated portion-wise with NBS (4.91 g, 27.6 mmol) over 30 min, stirred for 45 min, then concentrated to dryness. The residue was treated with EtOAc (8 mL), filtered to remove solids and purified via silica gel chromatography (EtOAc/Hex) to afford 5-bromo-6-ethylpyridin-2-amine (3.79 g, 68%). 1H NMR (400 MHz, DMSO-d6): δ 7.43 (d, J=8.6 Hz, 1 H), 6.21 (d, J=8.7 Hz, 1 H), 6.03 (s, 2 H), 2.61 (q, J=7.5 Hz, 2 H), 1.11 (t, J=7.5 Hz, 3 H);

Aufarbeitung

  1. concentrationconcentrated to dryness
  2. additionThe residue was treated with EtOAc (8 mL)
  3. filtrationfiltered
  4. customto remove solids
  5. custompurified via silica gel chromatography (EtOAc/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-e72a71d5539d48a28d2bf4a7eb264b21
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133183B2

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