2-Amino-3-Hydroxypyridine → 3-[(4-Methoxybenzyl)oxy]pyridin-2-amine

HRID 1654826Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1654826
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1.[NH2:11][C:12]1[C:17]([OH:18])=[CH:16][CH:15]=[CH:14][N:13]=1>[OH-].[Na+].ClCCl.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[NH2:11][C:12]1[C:17]([O:18][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:16][CH:15]=[CH:14][N:13]=1

Komponenten

7

Edukt 2

HCID 281142-Amino-3-HydroxypyridineHCID 1650214-Methoxybenzyl bromide

Produkt 1

HCID 27283893-[(4-Methoxybenzyl)oxy]pyridin-2-amineAusbeute 76,7 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 21218Trioctylmethylammonium chlorideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A mixture of 4-methoxybenzyl bromide (25 g, 0.159 mol) and 2-amino-3-hydroxypyridine (15.9 g, 0.145 mol) in 40% aqueous sodium hydroxide solution (150 ml) and dichloromethane (150 ml) was treated with Adogen 464 (5 ml) and stirred vigorously at room temperature for 16 hours. The mixture was diluted with further water and dichloromethane, the product extracted into dichloromethane, and the combined organic layers washed with water, dried and evaporated. The resulting solid was washed with ether to yield the product (25.6 g, 70%)

Aufarbeitung

  1. extractionthe product extracted into dichloromethane
  2. washthe combined organic layers washed with water
  3. customdried
  4. customevaporated
  5. washThe resulting solid was washed with ether

Quellen und Nachweise

ORD-Eintrag
ord-c45126958ef04d6a85f2ce607e71d9cf
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05409943

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