Acrylic Acid → (2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acid

HRID 18210

Reaktionsgleichung

Reaktionsgleichung von HRID 18210
[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[NH2:6][C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][N:8]=1.C([O-])([O-])=O.[Na+].[Na+]>O.Cl[Pd]Cl>[NH2:6][C:7]1[N:8]=[CH:9][C:10](/[CH:3]=[CH:2]/[C:1]([OH:5])=[O:4])=[CH:11][CH:12]=1

Komponenten

6

Edukt 3

HCID 6581Acrylic AcidHCID 10340Sodium CarbonateHCID 706222-Amino-5-bromopyridine

Produkt 1

HCID 10487224(2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acidAusbeute 62,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24290Palladium ChlorideKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

Acrylic acid (23 mL, 0.33 mole) was added carefully to a solution of 2-amino-5-bromopyridine (25.92 g, 0.15 mole) and Na2CO3 (55.64 g, 0.53 mole) in H2O (600 mL). PdCl2 (0.53 g, 0.003 mole) was then added, and the mixture was heated at reflux. After 24 hr, the reaction was cooled to RT and filtered, and the filtrate was adjusted to pH 6 with aqueous HCl. Additional H2O (0.5 L) was added to improve mixing, and the mixture was stirred for 1 hr. The pH was readjusted to 6, then the solid was collected by suction filtration. The filter pad was washed sequentially with H2O (2×0.5 L), cold absolute EtOH (100 mL), and Et2O (2×250 mL). Drying in high vacuum at elevated temperature gave the title compound (15.38 g, 62%) as a tan solid: 1H NMR (300 MHz, DMSO-d6) δ 8.11 (d, J=2.0 Hz, 1 H), 7.75 (dd, J=8.7, 2.0 Hz, 1 H), 7.43 (d, J=15.8 Hz, 1 H), 6.53 (s, 2 H), 6.45 (d, J=8.7 Hz, 1 H), 6.22 (d, J=15.8 Hz, 1 H); MS (ES) m/e 165 (M+H)+.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. filtrationfiltered
  4. additionAdditional H2O (0.5 L) was added
  5. additionto improve mixing
  6. filtrationthe solid was collected by suction filtration
  7. washThe filter pad was washed sequentially with H2O (2×0.5 L), cold absolute EtOH (100 mL), and Et2O (2×250 mL)
  8. customDrying in high vacuum at elevated temperature

Quellen und Nachweise

ORD-Eintrag
ord-e46d4c498b3e4c1bab7f03ef85e52ff7
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741339B2

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