Benzenepropanoic acid, 3-bromo-3-oxo-, ethyl ester → 6-(3-Bromophenyl)-4-hydroxy-2-(4-phenoxyphenyl)nicotinonitrile

HRID 81056Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 81056
[NH2:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)=[CH:3][C:4]#[N:5].[Br:19][C:20]1[CH:21]=[C:22]([C:26](=O)[CH2:27][C:28](OCC)=[O:29])[CH:23]=[CH:24][CH:25]=1>O>[Br:19][C:20]1[CH:21]=[C:22]([C:26]2[NH:1][C:2]([C:6]3[CH:11]=[CH:10][C:9]([O:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[CH:8][CH:7]=3)=[C:3]([C:4]#[N:5])[C:28](=[O:29])[CH:27]=2)[CH:23]=[CH:24][CH:25]=1

Komponenten

4

Edukt 2

HCID 179368Benzenepropanoic acid, 3-bromo-3-oxo-, ethyl esterHCID 669270523-Amino-3-(4-phenoxyphenyl)acrylonitrile

Produkt 1

HCID 669269356-(3-Bromophenyl)-4-hydroxy-2-(4-phenoxyphenyl)nicotinonitrileAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 3-amino-3-(4-phenoxyphenyl)acrylonitrile (0.553 g, 2342 mmol) and ethyl 3-(3-bromophenyl)-3-oxopropanoate (2.540 g, 9.37 mmol) was microwaved at 230° C. for 20 min. After cooling to room temperature, the mixture was diluted with water and extracted with ethyl acetate (100 mL). The ethyl acetate phase was washed with saturated ammonium chloride, brine, dried (MgSO4), and concentrated. Silica gel chromatography, eluting with 0-80% ethyl acetate in hexanes, gave 6-(3-bromophenyl)-4-oxo-2-(4-phenoxyphenyl)-1,4-dihydropyridine-3-carbonitrile as brown solid (0.909 g, 88% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.81 (1H, br. s), 7.70 (2H, δ, J=8.28 Hz), 7.62 (2H, δ, J=7.28 Hz), 7.35 (3H, t, J=7.40 Hz), 7.18 (1H, t, J=7.28 Hz), 7.03 (4H, dd, J=11.92, 8.66 Hz), 6.68 (1H, br. s); MS (ES+) m/z: 443,445 (M+H); LC retention time: 4.361 min (analytical HPLC Method A).

Aufarbeitung

  1. customwas microwaved at 230° C. for 20 min
  2. extractionextracted with ethyl acetate (100 mL)
  3. washThe ethyl acetate phase was washed with saturated ammonium chloride, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washSilica gel chromatography, eluting with 0-80% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-e21e7066e92442fd9454086db65fba2c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846673B2

Notizen zur Reaktion

Wird geladen…