Lithium Hydroxide → 3-Nitropyridine-2-carboxylic acid

HRID 370101

Reaction equation

HRID 370101 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

HCID 183766123-Nitropyridine-2-carboxylic acidYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-bc6e07d8479841b9a26da54b98fc628b
Source dataset
uspto-grants-2000_10
Patent number
US06140351

Linked notes

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