Triethylamine → 2-(2,4-Dimethoxybenzylamino)nicotinonitrile

HRID 271898

Reaktionsgleichung

Reaktionsgleichung von HRID 271898
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].C(N(CC)CC)C.Cl[C:21]1[N:28]=[CH:27][CH:26]=[CH:25][C:22]=1[C:23]#[N:24]>CN(C)C(=O)C>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5][NH:6][C:21]1[N:28]=[CH:27][CH:26]=[CH:25][C:22]=1[C:23]#[N:24]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 810792-ChloronicotinonitrileHCID 5972502,4-Dimethoxybenzylamine

Produkt 1

HCID 222931752-(2,4-Dimethoxybenzylamino)nicotinonitrileAusbeute 72,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2,4-Dimethoxybenzylamine (2.90 g, 17.3 mmol) and triethylamine (1.75 g, 17.3 mmol) were added sequentially to a solution of 2-chloronicotinonitrile (2.0 g, 14.4 mmol) in N,N-dimethylacetamide (29 mL). The reaction was heated at 80° C. for 4 h, quenched with water and extracted with diethyl ether (3×). The combined organic extracts were washed water, saturated brine, dried over magnesium sulfate and concentrated. The crude product was purified by flash chromatography (silica gel, 0-5% ethyl acetate (with 0.1 triethylamine) in dichloromethane gradient elution) to produce the title compound (2.80 g). MS 270.3 (M+1).

Aufarbeitung

  1. customquenched with water
  2. extractionextracted with diethyl ether (3×)
  3. washThe combined organic extracts were washed water, saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography (silica gel, 0-5% ethyl acetate (with 0.1 triethylamine) in dichloromethane gradient elution)

Quellen und Nachweise

ORD-Eintrag
ord-b7245b92988a462c90e8b9cdb0bb8f22
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452903B2

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