Sodium Hydroxide → 2-methyl-2-(5'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-propionic acid

HRID 557696Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 557696
C([O:3][C:4](=[O:23])[C:5]([CH3:22])([CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][N:14]=2)[CH2:9][CH2:8]1)[CH3:6])C.[OH-].[Na+]>O1CCCC1.CO>[CH3:22][C:5]([CH:7]1[CH2:8][CH2:9][N:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][N:14]=2)[CH2:11][CH2:12]1)([CH3:6])[C:4]([OH:23])=[O:3]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 667385542-methyl-2-(5'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-propionic acid ethyl ester

Produkt 1

HCID 667384112-methyl-2-(5'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-propionic acidAusbeute 71,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a solution of 2-methyl-2-(5′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-propionic acid ethyl ester (321 mg, 1.0 mmol) in tetrahydrofuran (2 mL) and methanol (6 mL) was added sodium hydroxide solution (1N, 2 mL). The mixture was heated in a microwave at 140° C. for 1.5 hr. The mixture was evaporated and the residue was dissolved in hot methanol and water. The clear solution was then acidified with 1N hydrochloric acid (2.5 mL). The resulting pale yellow precipitate was filtered and dried to give 2-methyl-2-(5′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-propionic acid (210 mg). LC-MS calcd. for C14H19N3O4 (m/e) 293.1, obsd 294.1

Aufarbeitung

  1. customThe mixture was evaporated
  2. dissolutionthe residue was dissolved in hot methanol
  3. filtrationThe resulting pale yellow precipitate was filtered
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9730d43f4a874cd49eb9af7e2af23f55
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058299B2

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