Lithium Hydroxide → 3-Nitropyridine-2-carboxylic acid

HRID 370101

Reaktionsgleichung

Reaktionsgleichung von HRID 370101
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 %

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 1N 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 1N 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-bc6e07d8479841b9a26da54b98fc628b
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06140351

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