2-Chloro-3-pyridylamine → HCID 64507477, Verbindung

HRID 1419068Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1419068
[NH2:1][C:2]1[C:3]([Cl:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:9][C:10]1([CH3:21])[CH2:14][C:13]2[CH:15]=[CH:16][CH:17]=[C:18]([CH:19]=O)[C:12]=2[O:11]1>C(O)(=O)C>[CH3:9][C:10]1([CH3:21])[CH2:14][C:13]2[CH:15]=[CH:16][CH:17]=[C:18]([CH2:19][NH:1][C:2]3[C:3]([Cl:8])=[N:4][CH:5]=[CH:6][CH:7]=3)[C:12]=2[O:11]1

Komponenten

4

Edukt 2

HCID 805282-Chloro-3-pyridylamineHCID 27954712,2-Dimethyl-2,3-dihydro-1-benzofuran-7-carbaldehyde

Produkt 1

HCID 64507477HCID 64507477, VerbindungAusbeute 108,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

5 g of 3-amino-2-chloropyridine was dissolved in 80 ml of acetic acid, and 7.1 g of 2,2-dimethyl-7-formyl-2,3-dihydrobenzofuran was added. Then, the mixture was stirred at room temperature for about 30 minutes, and 16.5 g of triacetoxy sodium borohydride was added gradually under ice-cooling. After stirring the obtained reaction mixture at room temperature for about four hours, the solvent was concentrated. After adding ice-water to the residue and alkalizing it with an aqueous sodium hydroxide solution, it was extracted twice with ethyl acetate. After washing the organic layer with water and drying, it was concentrated and purified with a short column (dichloromethane/methanol=10:1) using silica gel to obtain 12.2 g of oily 3-[(2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methyl]amino-2-chloropyridine.

Aufarbeitung

  1. temperaturecooling
  2. stirringAfter stirring
  3. customthe obtained reaction mixture at room temperature for about four hours
  4. concentrationthe solvent was concentrated
  5. additionAfter adding ice-water to the residue
  6. extractionwas extracted twice with ethyl acetate
  7. washAfter washing the organic layer with water
  8. customdrying
  9. concentrationit was concentrated
  10. custompurified with a short column (dichloromethane/methanol=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-103a776c76904debb41291eff76c46d7
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05886011

Notizen zur Reaktion

Wird geladen…