Triethylamine → Ethyl 2-(E-2-(4-(N,N-dimethylaminomethyl)phenyl)ethen-1-yl)nicotinate

HRID 1178192

Reaktionsgleichung

Reaktionsgleichung von HRID 1178192
Cl[C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:13][N:14]([CH2:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[CH2:22])=[CH:19][CH:18]=1)[CH3:15].C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:15][N:14]([CH2:16][C:17]1[CH:18]=[CH:19][C:20](/[CH:21]=[CH:22]/[C:2]2[N:12]=[CH:11][CH:10]=[CH:9][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:23][CH:24]=1)[CH3:13]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 519956Benzenemethanamine, ar-ethenyl-N,N-dimethyl-HCID 2796614Ethyl chloronicotinate

Produkt 1

HCID 11811059Ethyl 2-(E-2-(4-(N,N-dimethylaminomethyl)phenyl)ethen-1-yl)nicotinateAusbeute 33,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

6.7 g (39 mmol) of ethyl 2-chloronicotinate, 8.2 g (51 mmol) of 4-(N,N-dimethylaminomethyl)styrene, 9.9 g (98 mmol) of triethylamine, 0.36 g of palladium(II) acetate and 0.96 [lacuna] of tri(o-tolyl)phosphine were mixed in 150 ml of dimethylformamide and, after addition of 1 ml of water, stirred at 140° C. for 13 h. The reaction mixture was then concentrated in vacuo, and the resulting residue was partitioned between ethyl acetate and water. The organic phase was separated off, washed with water, dried and concentrated in vacuo. The residue was then crystallized as oxalate from isopropanol after addition of an equivalent amount of oxalic acid. 4.1 g (27%) of the product were obtained as monooxalate.

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe resulting residue was partitioned between ethyl acetate and water
  3. customThe organic phase was separated off
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was then crystallized as oxalate from isopropanol
  8. additionafter addition of an equivalent amount of oxalic acid

Quellen und Nachweise

ORD-Eintrag
ord-7cb28733a5ff47dbacee37355451ca60
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276500B2

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