3-Cyano-2,6-dichloro-4-methylpyridine → (E)-2,6-Dichloro-4-(2-(dimethylamino)vinyl)nicotinonitrile

HRID 1034943

Reaktionsgleichung

Reaktionsgleichung von HRID 1034943
[Cl:1][C:2]1[N:9]=[C:8]([Cl:10])[CH:7]=[C:6]([CH3:11])[C:3]=1[C:4]#[N:5].CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>C(O)(C)C>[Cl:1][C:2]1[N:9]=[C:8]([Cl:10])[CH:7]=[C:6](/[CH:11]=[CH:14]/[N:15]([CH3:17])[CH3:16])[C:3]=1[C:4]#[N:5]

Komponenten

4

Edukt 2

HCID 701313-Cyano-2,6-dichloro-4-methylpyridineHCID 78373Dimethylformamide dimethyl acetal

Produkt 1

HCID 58093913(E)-2,6-Dichloro-4-(2-(dimethylamino)vinyl)nicotinonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To 2,6-dichloro-4-methylnicotinonitrile (20.3 g, 0.108 mol) in 200 mL of isopropyl alcohol is added N,N-dimethylformamide dimethylacetal (14.4 mL, 0.108 mol) and the reaction is stirred at 65° C. for 18 hrs. After the reaction is cooled to ambient temperature, the precipitate is collected by filtration, washed with 50 mL of isopropyl alcohol, and air dried giving (E)-2,6-Dichloro-4-(2-(dimethylamino)vinyl)nicotinonitrile as a yellow solid. MS (ES+) calcd. 242.02. found 242.10 (MH+). H-NMR (600 MHz, DMSO-d6) 2.90 (br.s, 3H), 3.17 (br.s, 3H), 5.05 (d, J=12.6 Hz, 1H), 7.61 (s, 1H), 8.09 (d, J=12.6 Hz, 1H).

Aufarbeitung

  1. temperatureAfter the reaction is cooled to ambient temperature
  2. filtrationthe precipitate is collected by filtration
  3. washwashed with 50 mL of isopropyl alcohol, and air
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-6a049bcd94eb4f10a1237941cfb83371
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546370B2

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