Ammonia → Methyl 3-amino-3-(pyridin-3-yl)prop-2-enoate

HRID 1058097

Reaktionsgleichung

Reaktionsgleichung von HRID 1058097
[C:1]([CH2:9][C:10]([O:12][CH3:13])=[O:11])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.C(O)(C)C.C(O)=O.[NH3:21]>C1(C)C=CC=CC=1>[NH2:21][C:1]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[CH:9][C:10]([O:12][CH3:13])=[O:11]

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 284Formic AcidHCID 3776IsopropanolHCID 1086453-Pyridinepropanoic acid, beta-oxo-, methyl ester

Produkt 1

HCID 69944552Methyl 3-amino-3-(pyridin-3-yl)prop-2-enoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

Methyl nicotinoylacetate (88 g, 0.5 mol) was dissolved in toluene (200 g), isopropyl alcohol (200 g), and formic acid (98-100%, 1.22 g, 0.03 mol) and heated to 60-65° C. Gaseous ammonia (23 g, 1.35 mol) was bubbled through the solution for 15 minutes. The white suspension was stirred at 65° C. until a homogeneous solution formed. The solution was stirred for two hours at 65° C. and then concentrated (ca. 200 g) at 65° C. The residue was cooled to −5° C. with stirring and methyl 3-amino-3-(3-pyridyl)-2-propenoate crystallized as colorless needles. The process of reducing the volume to 50% followed by cooling was repeated three times with the mother liquors. Filtration, washing with toluene, and drying at 30° C. resulted in 77.74 g (88.8%) of methyl 3-amino-3-(3-pyridyl)-2-propenoate as colorless crystals.

Aufarbeitung

  1. customformed
  2. stirringThe solution was stirred for two hours at 65° C.
  3. concentrationconcentrated (ca. 200 g) at 65° C
  4. temperatureThe residue was cooled to −5° C.
  5. stirringwith stirring
  6. custommethyl 3-amino-3-(3-pyridyl)-2-propenoate crystallized as colorless needles
  7. temperatureby cooling
  8. filtrationFiltration
  9. washwashing with toluene
  10. customdrying at 30° C.
  11. customresulted in 77.74 g (88.8%) of methyl 3-amino-3-(3-pyridyl)-2-propenoate as colorless crystals

Quellen und Nachweise

ORD-Eintrag
ord-3fa5e721e718439b9d7e1fad80c683ca
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06515130B1

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