Water → 2-Amino-3-(2-chloro-4,5-methylenedioxybenzyloxy)-pyridine

HRID 1654837

Reaktionsgleichung

Reaktionsgleichung von HRID 1654837
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:9]1[O:13][C:12]2[CH:14]=[C:15]([Cl:20])[C:16]([CH2:18]Cl)=[CH:17][C:11]=2[O:10]1.O>ClCCl.[OH-].[Na+].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[NH2:1][C:2]1[C:7]([O:8][CH2:18][C:16]2[CH:17]=[C:11]3[O:10][CH2:9][O:13][C:12]3=[CH:14][C:15]=2[Cl:20])=[CH:6][CH:5]=[CH:4][N:3]=1

Komponenten

7

Edukt 3

HCID 962WaterHCID 281142-Amino-3-HydroxypyridineHCID 901136-Chloropiperonyl chloride

Produkt 1

HCID 200770492-Amino-3-(2-chloro-4,5-methylenedioxybenzyloxy)-pyridineAusbeute 24,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 21218Trioctylmethylammonium chlorideKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-3-hydroxypyridine (9.75 g, 0.0886 mol) in dichloromethane (55 ml) and 40% sodium hydroxide (55 ml) was added Adogen 464 (5 ml) and 6-chloropiperonyl chloride (20 g, 0,0975 mol) with vigorous stirring. The mixture was stirred at room temperature for 16 hours. Water (55 ml) was added and the mixture extracted with dichloromethane. The combined organic layers were dried and evaporated, and the residue purified by flash chromatography (silica, 1% methanol/dichloromethane) and trituration with ether to yield the title compound (6 g), m.p. 100°-104° C.

Aufarbeitung

  1. extractionthe mixture extracted with dichloromethane
  2. customThe combined organic layers were dried
  3. customevaporated
  4. customthe residue purified by flash chromatography (silica, 1% methanol/dichloromethane) and trituration with ether

Quellen und Nachweise

ORD-Eintrag
ord-c18b5067f4074f708abea2967a7af022
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05409943

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