Water → 2-Nitro-5-(2-quinolylmethoxy)benzyl alcohol

HRID 1721684

Reaktionsgleichung

Reaktionsgleichung von HRID 1721684
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH2:7][OH:8].O.[F-].C([N+](CC)(CC)CC)C.Cl[CH2:25][C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=1.O>CN(C=O)C>[N+:10]([C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:25][C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=2)=[CH:9][C:6]=1[CH2:7][OH:8])([O-:12])=[O:11]

Komponenten

6

Edukt 4

HCID 962WaterHCID 203942-(Chloromethyl)quinolineHCID 1089463-(Hydroxymethyl)-4-nitrophenolHCID 16211652Tetraethylammonium fluoride hydrate

Produkt 1

HCID 106148772-Nitro-5-(2-quinolylmethoxy)benzyl alcoholAusbeute 33,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 5-hydroxy-2-nitrobenzyl alcohol (5.1 g, 30 mmol), tetraethylammonium fluoride hydrate (8.94 g, 60 mmol) and 2-chloromethylquinoline (5.31 g, 30 mmol) in DMF (90 ml) was stirred at room temperature for 72 hours. The reaction mixture was then poured into water and extracted with ethyl acetate. The extract was dried over MgSO4 and concentrated in vacuo. To the residue was added methylene chloride (25 ml) and the solid was filtered to provide 3.1 g of 2-nitro-5-(2-quinolylmethoxy)benzyl alcohol.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. additionTo the residue was added methylene chloride (25 ml)
  5. filtrationthe solid was filtered

Quellen und Nachweise

ORD-Eintrag
ord-f345799dcf9c49f0851569fcf72688c4
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05512581

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