Sodium Hydroxide → 4-Methoxy-5-methoxycarbonyl-nicotinic acid

HRID 6895Notes

Reaction equation

HRID 6895 reaction equation
C[O:2][C:3](=[O:16])[C:4]1[C:9]([O:10][CH3:11])=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:7]=[N:6][CH:5]=1.[OH-].[Na+]>CO.O>[CH3:11][O:10][C:9]1[C:4]([C:3]([OH:16])=[O:2])=[CH:5][N:6]=[CH:7][C:8]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22019197Methyl-4-methoxy-5-methoxycarbonyl-nicotinate

Product 1

HCID 220191954-Methoxy-5-methoxycarbonyl-nicotinic acidYield 57%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 5,3 g (23.5 mmol) of methyl-4-methoxy-5-methoxycarbonyl-nicotinate in 150 ml of methanol and 50 m. of water is added a solution of 0.94 g (23,5 mmol) of sodium hydroxide in 10 ml of water. The resulting mixture is stirred at room temperature overnight. The methanol is removed under vacuum, the aqueous solution is made slightly acidic and extracted with ethyl acetate. The combined organic phases are dried and filtered through silica. The filtrate is evaporated to near dryness and diluted with diisopropyl ether. A precipitate is obtained, filtered off and dried. There is obtained 2,83 g (57% yield) of a white solid (M+1=212).

Workup

  1. customThe methanol is removed under vacuum
  2. extractionextracted with ethyl acetate
  3. customThe combined organic phases are dried
  4. filtrationfiltered through silica
  5. customThe filtrate is evaporated
  6. additiondiluted with diisopropyl ether
  7. customA precipitate is obtained
  8. filtrationfiltered off
  9. customdried

Sources & evidence

ORD record
ord-5e8c5e49e9bb4710b4cc40f382d88cd5
Source dataset
uspto-grants-2006_08
Patent number
US07084163B2

Reaction notes

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