Lithium Hydroxide → 3-Nitropyridine-2-carboxylic acid

HRID 844170

Reaktionsgleichung

Reaktionsgleichung von HRID 844170
C([O:3][C:4]([C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][N:7]=1)=[O:5])C.[OH-].[Li+]>CO.O>[C:4]([C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][N:7]=1)([OH:5])=[O:3]

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 18376573Ethyl 3-nitropyridine-2-carboxylate

Produkt 1

HCID 183766123-Nitropyridine-2-carboxylic acidAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 2-ethoxycarbonyl-3-nitropyridine (0.5 g, 2.5 mmol, 1 eq.) in 20 mL of methanol and 5 mL of water was added lithium hydroxide (0.2 g, 4.5 mmol, 1.8 eq.) and the mixture stirred for 16 hours at ambient temperature. The reaction was concentrated and 50 mL of 1 N KOH was were added. The solution was washed with 25 mL of ethyl actetate, acidified with 1 N HCl, and extracted with ethyl acetate (3×50 mL). The combined ethyl acetate extractions were dried over sodium sulfate and concentrated to give 2-carboxy-3-nitropyridine as a yellow solid (0.4 g, 95% yield).

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. addition50 mL of 1 N KOH was were added
  3. washThe solution was washed with 25 mL of ethyl actetate
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. extractionThe combined ethyl acetate extractions
  6. dry with materialwere dried over sodium sulfate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-096478117006417c96428ac8a4cffbb4
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06380221B1

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