p-Toluenesulfonic acid → 2-Pentenoic acid, 3-(3-pyridinylamino)-, methyl ester, (Z)-

HRID 893618

Reaktionsgleichung

Reaktionsgleichung von HRID 893618
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C[CH2:9][CH2:10][C:11]([CH2:13][C:14]([O-:16])=[O:15])=O.[C:17]1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC>[CH3:17][O:16][C:14](=[O:15])/[CH:13]=[C:11](\[NH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)/[CH2:10][CH3:9]

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 100093-AminopyridineHCID 119662643-Oxohexanoate

Produkt 1

HCID 198908032-Pentenoic acid, 3-(3-pyridinylamino)-, methyl ester, (Z)-Ausbeute 467,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A mixture of 3-aminopyridine (5.0 g), methylpropionylacetate (7.6 g) and p-toluenesulphonic acid (0.5 g) was stirred for 96 hours and then ether (100 ml) was added. The solution was washed with water (100 ml) and dried (MgSO4). The solvent was removed by evaporation and the residue purified by flash chromatography, eluting with ethyl acetate to give methyl-(Z)-3-(3-pyridylamino)-2-pentenoate (B3) (2.8 g) as an oil; NMR (CDCl3): 1.1(t,3H), 2.5(q,2H), 3.7(s,3H), 4.95(s,1H), 7.3(m,1H), 7.4(m,1H), 8.4(m,2H), 10.3(br,1H).

Aufarbeitung

  1. washThe solution was washed with water (100 ml)
  2. dry with materialdried (MgSO4)
  3. customThe solvent was removed by evaporation
  4. customthe residue purified by flash chromatography
  5. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-d221c66ba92248faba65111fab6dcb1d
Quelldatensatz
uspto-grants-1992_06
Patentnummer
US05126344

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