Sodium Hydroxide → 6-Chloro-5-ethylpyridin-2-amine

HRID 2188896Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2188896
[Cl:1][C:2]1[N:7]=[C:6]([NH:8]C(=O)C(C)(C)C)[CH:5]=[CH:4][C:3]=1[CH2:15][CH3:16].[OH-].[Na+]>Cl>[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[CH2:15][CH3:16]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 59272532N-(6-chloro-5-ethylpyridin-2-yl)pivalamide

Produkt 1

HCID 591659856-Chloro-5-ethylpyridin-2-amineAusbeute 86,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

A suspension of N-(6-chloro-5-ethylpyridin-2-yl)pivalamide (1.16 g, 4.82 mmol) in 6N HCl (20 mL) was heated at reflux overnight. The reaction mixture was cooled to room temperature and was treated with aqueous NaOH to pH 8. The aqueous layer was extracted with EtOAc. The organic layer was dried over MgSO4 and the solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel (5% EtOAc in petroleum ether) to afford 6-chloro-5-ethylpyridin-2-amine (650 mg, 86%). 1H NMR (CDCl3, 400 MHz) δ 7.35 (d, J=8.4, 1H), 6.45 (d, J=8.4, 1H), 2.61 (q, J=7.6, 2H), 1.18 (t, J=7.6, 3H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was purified by chromatography on silica gel (5% EtOAc in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-c71aac0edebc41908ef00bcfb7d8d4cd
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324207B2

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