Sodium Hydroxide → 2-Butoxy-6-methylpyridin-4-amine

HRID 2192997Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2192997
Cl[C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[OH-:10].[Na+]>C(O)CCC.O>[CH2:9]([O:10][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([CH3:9])[N:3]=1)[CH2:4][CH2:5][CH3:6]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 126437072-Chloro-6-methylpyridin-4-amine

Produkt 1

HCID 593754742-Butoxy-6-methylpyridin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2631-ButanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

2-chloro-6-methylpyridin-4-amine (36 g, 0.25 mol) and sodium hydroxide (24 g, 1 mol) were dissolved in 1-butanol (400 mL). The solution was heated at reflux for 10 h, and then cooled to rt. The reaction mixture was diluted with water (300 mL) and then extracted with ethyl acetate (3×500 mL). The combined organic layers were washed with brine (500 mL), dried over sodium sulfate, and concentrated to afford 2-butoxy-6-methylpyridin-4-amine. 1H NMR (400 MHz, CDCl3) δ 6.05 (d, J=0.6 Hz, 1H), 5.75 (d, J=0.6 Hz, 1H), 4.18 (t, J=6.4 Hz, 1H), 2.30 (s, 3H), 1.71 (m, 2H), 1.48 (m, 2H), 0.98 (t, J=7.6 Hz, 3H). LRMS calc'd for (C10H16N2O) [M+H]+, 181; found 181.

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureat reflux for 10 h
  3. extractionextracted with ethyl acetate (3×500 mL)
  4. washThe combined organic layers were washed with brine (500 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c6dd2203070646789140481cdaf85526
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329722B2

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