6-Methoxy-3-pyridinylamine → HCID 178471946, Verbindung

HRID 526153

Reaktionsgleichung

Reaktionsgleichung von HRID 526153
C(O[CH:4]=[C:5]([C:11](=[O:13])[CH3:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][N:17]=1>ClC1C=CC=CC=1>[CH3:14][O:15][C:16]1[N:17]=[CH:18][C:19]([NH:22][CH:4]=[C:5]([C:11](=[O:13])[CH3:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:20][CH:21]=1

Komponenten

4

Edukt 2

HCID 811216-Methoxy-3-pyridinylamineHCID 97734Butanoic acid, 2-(ethoxymethylene)-3-oxo-, ethyl ester

Produkt 1

HCID 178471946HCID 178471946, VerbindungAusbeute 84,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7964ChlorobenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

A mixture of ethyl 2-(ethoxymethylene)-3-oxobutanoate (100 g, 0.54 mol) and 2-methoxy-5-aminopyridine (67 g, 0.54 mol) in chlorobenzene (500 mL) was heated at 135° C. for 4 h in a round bottomed flask that was equipped with a distillation apparatus to collect the ethanol generated during the reaction. The reaction mixture was cooled and concentrated and the residue was triturated in diethylether and filtered to obtain the desired product (120 g, 84%) as an off-white solid: 1H NMR (500 MHz, CDCl3) δ 12.74 (d, 12.3 Hz, 1H), 8.35 (d, J=13.0 Hz, 1H), 8.07 (d, J=2.8 Hz, 1H), 7.55 (d, J=8.8, 2.9 Hz, 1H), 6.79 (d, J=8.8 Hz, 1H), 4.30 (q, J=7.1 Hz, 2H), 2.55 (s, 3H), 1.33 (t, J=7.1 Hz, 1H); ESI MS m/z 265 [M+H]+.

Aufarbeitung

  1. customwas equipped with a distillation apparatus
  2. customto collect the ethanol
  3. customgenerated during the reaction
  4. temperatureThe reaction mixture was cooled
  5. concentrationconcentrated
  6. customthe residue was triturated in diethylether
  7. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-dd98bd0e315e41bbbf0477496d67e4b3
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09345709B2

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