Water → 2-Fluoro-6-[(2-methoxyethyl)amino]benzonitrile

HRID 897589Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 897589
F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[C:4]#[N:5].COC[CH2:14][CH2:15][NH2:16].[C:17](=[O:20])([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([NH:16][CH2:15][CH2:14][O:20][CH3:17])[C:3]=1[C:4]#[N:5]

Komponenten

6

Edukt 4

HCID 962WaterHCID 16723-MethoxypropylamineHCID 11430Potassium CarbonateHCID 746952,6-Difluorobenzonitrile

Produkt 1

HCID 223466972-Fluoro-6-[(2-methoxyethyl)amino]benzonitrileAusbeute 71,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2,6 difluorobenzonitrile (3.5 g, 25.16 mmol) in dimethylformamide (50 mL) was treated with 3-methoxypropylamine (2.24 g, 25.16 mmol) and potassium carbonate (6.94 g, 50.32 mmol). The reaction mixture was stirred over night under a nitrogen atmosphere. Water (100 mL) was added to the reaction solution. The layers were partitioned, and the aqueous layer was extracted with ethyl acetate (1.2 L). The combined organic layers were washed with water (1.5 L), dried over magnesium sulfate, filtered, and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel using 7:1 heptane:ethyl acetate as the eluent. The column afforded 3.5 g (68%) of 2-fluoro-6-[(2-methoxyethyl)amino]benzonitrile. 1H NMR (DMSO-d6, 400 MHz) δ 7.48-7.39 (m, 1H), 6.64-6.48 (m, 2H), 3.45-3.31 (m, 2H), 3.30-3.20 (m, 5H), 1.85-1.75 (m, 2H); HPLC Waters 2690 Alliance HPLC (Symmetry Shield RP18 3.5 μm, 2.1×50 mm; 5%-95% acetonitrile-0.1 M ammonium acetate over 15 min, 0.5 mL/min) Rt 6.57 min (97%).

Aufarbeitung

  1. customThe layers were partitioned
  2. extractionthe aqueous layer was extracted with ethyl acetate (1.2 L)
  3. washThe combined organic layers were washed with water (1.5 L)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe crude product was purified by flash chromatography on silica gel using 7:1 heptane

Quellen und Nachweise

ORD-Eintrag
ord-7cc4c5a5b6944421acf0071ecf8ac517
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06921763B2

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