Water → 4-((2,2-Dimethyl-1,3-dioxolan-4-yl)methoxy)pyridin-2-amine

HRID 79436

Reaktionsgleichung

Reaktionsgleichung von HRID 79436
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[CH3:9][C:10]1([CH3:17])[O:14][CH:13]([CH2:15][OH:16])[CH2:12][O:11]1.[Na].O>ClCCl>[CH3:9][C:10]1([CH3:17])[O:14][CH:13]([CH2:15][O:16][C:2]2[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=2)[CH2:12][O:11]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7528SolketalHCID 5818662-Amino-4-chloropyridineHCID 5360545Sodium

Produkt 1

HCID 509875954-((2,2-Dimethyl-1,3-dioxolan-4-yl)methoxy)pyridin-2-amineAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
145 °C

Versuchsvorschrift

A sealed tube containing 4-chloro-2-pyridinamine (4 g, 31.2 mmol), (2,2-dimethyl-1,3-dioxolan-4-yl)methanol (8.4 g, 60.6 mmol), and sodium (1.46 g, 63.5 mmol) was heated at 145° C. for 8 hours. The mixture was cooled to ambient temperature; water (25 mL) and dichloromethane (50 mL) were added. The organic phase was separated, dried with sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by chromatography on silica-gel to give 4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)pyridin-2-amine as a pale yellow solid (5.6 g).

Aufarbeitung

  1. temperatureThe mixture was cooled to ambient temperature
  2. customThe organic phase was separated
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography on silica-gel

Quellen und Nachweise

ORD-Eintrag
ord-5231720e43f441fda1d0c65964eaca65
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841455B2

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