3-Hydroxybenzyl alcohol → 6-(3-Hydroxymethyl-phenoxy)-nicotinonitrile

HRID 2266987

Reaktionsgleichung

Reaktionsgleichung von HRID 2266987
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].C(=O)([O-])[O-].[K+].[K+].[CH:16]1[C:21]([C:22]#[N:23])=[CH:20][N:19]=[C:18](Cl)[CH:17]=1.O>CC(N(C)C)=O>[OH:6][CH2:5][C:4]1[CH:3]=[C:2]([CH:9]=[CH:8][CH:7]=1)[O:1][C:18]1[CH:17]=[CH:16][C:21]([C:22]#[N:23])=[CH:20][N:19]=1

Komponenten

6

Edukt 4

HCID 1023-Hydroxybenzyl alcoholHCID 962WaterHCID 11430Potassium CarbonateHCID 51520946-Chloro-3-pyridinecarbonitrile

Produkt 1

HCID 616796946-(3-Hydroxymethyl-phenoxy)-nicotinonitrileAusbeute 99,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Add 3-hydroxybenzyl alcohol (0.99 g, 7.94 mmol) and potassium carbonate (1.50 g, 10.83 mmol) to 6-chloronicotinitrile (1.00 g, 7.22 mmol) in dimethylacetamide (25 mL) and stir. Heat to 100° C. for 4 hrs. Let cool to ambient temperature and pour into water (100 mL). Extract with diethyl ether (3×100 mL). Combine the organic layers and wash with 1N NaOH (2×50 mL) and dry over magnesium sulfate. Filter and concentrate under reduced pressure to give the product (1.63 g, 99%): 1H NMR (CDCl3) 8.49 (d, J=2.2 Hz, 1H), 7.95 (dd, J=2.2 Hz, 8.7 Hz, 1H), 7.47 (t, J=7.9 Hz, 1H), 7.29 (s, 1H), 7.21 (s, 1H), 7.10 (d, J=8.2 Hz, 1H), 7.06 (d, J=8.7 Hz, 1H), 4.77 (s, 2H).

Aufarbeitung

  1. temperatureLet cool to ambient temperature
  2. extractionExtract with diethyl ether (3×100 mL)
  3. washCombine the organic layers and wash with 1N NaOH (2×50 mL)
  4. dry with materialdry over magnesium sulfate
  5. filtrationFilter
  6. concentrationconcentrate under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7a5efea959f2426a8b28d0f0c0cde306
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858646B2

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