Ammonium Hydroxide → 2-Amino-6-(4,5-dihydrofuran-2-yl)benzonitrile

HRID 711806Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 711806
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6](Br)[C:3]=1[C:4]#[N:5].[O:11]1[CH2:15][CH2:14][CH:13]=[C:12]1[Sn](C)(C)C.[Cl-].[NH4+].[OH-].[NH4+]>C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([C:12]2[O:11][CH2:15][CH2:14][CH:13]=2)[C:3]=1[C:4]#[N:5]

Komponenten

7

Edukt 4

HCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 98130382-Amino-6-bromobenzonitrileHCID 10243055(4,5-Dihydrofuran-2-yl)trimethylstannane

Produkt 1

HCID 667461322-Amino-6-(4,5-dihydrofuran-2-yl)benzonitrileAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

2-Amino-6-bromobenzonitrile (0.75 g, 3.81 mmol), (4,5-dihydrofuran-2-yl)trimethylstannane (Menez, P.; Fargeas, V.; Poisson, J.; Ardisson, J.; Lallemand, J.-Y.; Pancrazi, A. Tetrahedron Letters 1994, 35(42), 7767) (1.02 g, 4.38 mmol), and palladium tetrakis(triphenylphosphine) (0.33 g, 0.28 mmol) were refluxed in toluene (10.0 mL) under nitrogen for 1.5 h. Saturated ammonium chloride (12 mL) and ammonium hydroxide (4 mL) were added, and the mixture was extracted with EtOAc. The organic layer was concentrated under vacuum and the residue was purified by chromatography on silica using 35% EtOAc/hexanes to give 0.48 g (68%) of the title compound as yellow oil. 1H NMR (400 MHz, Acetone-d6) δ 2.78-2.83 (m, 2H), 4.40 (t, J=9.2 Hz, 2H), 5.76 (t, J=3.2 Hz, 1H), 6.04 (s, 2H), 6.77-6.80 (m, 2H), 7.28 (t, J=8.0 Hz, 1H). MS 187 (MH+).

Aufarbeitung

  1. extractionthe mixture was extracted with EtOAc
  2. concentrationThe organic layer was concentrated under vacuum
  3. customthe residue was purified by chromatography on silica using 35% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-31dc5fb6aa984e72a3244adf56965e18
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181276B2

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