Pyridine → Ethyl 4-(3-naphthalen-2-yl-acryloylamino)benzoate

HRID 2422936Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2422936
N1C=CC=CC=1.[NH2:7][C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=1.[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]=1/[CH:29]=[CH:30]/[C:31](Cl)=[O:32]>C(Cl)Cl>[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]=1[CH:29]=[CH:30][C:31]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:17][CH:18]=1)=[O:32]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 2337BenzocaineHCID 11830880(E)-3-(2-naphthyl)propenoyl chloride

Produkt 1

HCID 67243223Ethyl 4-(3-naphthalen-2-yl-acryloylamino)benzoateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Anhydrous pyridine (0.331 g, 4.2 mmol, 1.2 eq) and ethyl 4-aminobenzoate (0.577 g, 3.50 mmol) were added to a solution of (E)-3-(2-naphthyl)propenoyl chloride (prepared from its corresponding acid) (0.757 g, 3.50 mmo) in anhydrous DCM (15 ml) under Ar. After stirring overnight at room temperature, the white precipitate was filtered, washed with DCM (10 ml) and dried under vacuum to give the amide 42 (0.960 g, 2.78 mmol, 80%) as a white solid, mp 173-175° C. 1H NMR (400 MHz, DMSO-d6) δ 1.30 (3H, t, J 7.2 Hz), 4.28 (2H, t, J 7.2 Hz), 6.97 (1H, d, J 15.4 Hz), 7.54-7.57 (2H, m), 7.7 (1H, d, J 15.4 Hz), 7.77 (1H, dd, J 1.6, 9.2 Hz), 7.84 (2H, d, J 8.8 Hz), 7.93-7.97 (5H, m), 8.15 (1H, s), 10.58 (1H, bs). 13C NMR (100 MHz, DMSO-d6) δ 14.88, 61.09, 119.30, 122.91, 124.18, 124.99, 127.47, 127.83, 128.38, 129.09, 129.36, 130.05, 130.98, 132.82, 133.68, 134.26, 141.64, 144.33, 164.69, 166.01. νmax (solid)/(cm−1) 3357, 1702, 1660, 1619, 1607, 1591, 1521, 1403, 1282. MS (API-ES): m/z 346 [M+H]+ (100%), HRMS (API-ES) m/z found 346.1443 [M+H]+.

Aufarbeitung

  1. filtrationthe white precipitate was filtered
  2. washwashed with DCM (10 ml)
  3. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-114f9e51929f4924a34c69cf59a14a9d
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960434B2

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