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

HRID 1442899Notes

Reaction equation

HRID 1442899 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 ml 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-d6079ad4ea5a4e8b956905e2fb6591a3
Source dataset
uspto-grants-2010_02
Patent number
US07659307B2

Reaction notes

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