Hydrochloric Acid → 7-[(2-Chloropyridin-4-yl)oxy]-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

HRID 1640200

Reaktionsgleichung

Reaktionsgleichung von HRID 1640200
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([C:12]([OH:14])=[O:13])[CH2:9]2)=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:21]=[C:20]([N+]([O-])=O)[CH:19]=[CH:18][N:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C=O)C>[Cl:15][C:16]1[CH:21]=[C:20]([O:1][C:2]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][CH:8]([C:12]([OH:14])=[O:13])[CH2:9]3)=[CH:4][CH:3]=2)[CH:19]=[CH:18][N:17]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 7351522-Chloro-4-nitropyridineHCID 145412687-Hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

Produkt 1

HCID 580552117-[(2-Chloropyridin-4-yl)oxy]-1,2,3,4-tetrahydronaphthalene-2-carboxylic acidAusbeute 52,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 7-hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (5.62 g, 29.2 mmol); 2-chloro-4-nitropyridine (5.10 g, 32.2 mmol) and cesium carbonate (28.6 g, 87.7 mmol) in DMF (150 mL) was heated at 50° C. for 5 hr. The reaction mixture was allowed to cool to rt and acidified to pH 3 by addition of 1N HCl. The mixture was extracted with EtOAc and the organic solutions were combined, washed with water, dried over Na2SO4 and evaporated. The residue was adsorbed onto silica and purified by filtration through a pad of silica. The product was then triturated with EtOAc to give 7-[(2-chloropyridin-4-yl)oxy]-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (4.62 g, 52.0%). LCMS: (FA) ES+ 304.1, ES− 302.1.

Aufarbeitung

  1. extractionThe mixture was extracted with EtOAc
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. filtrationpurified by filtration through a pad of silica
  6. customThe product was then triturated with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-bf3a1acc90354465b1e8cdbb4a1fe2ab
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110687B2

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