2-(3-Methoxycarbonyl-phenoxy)-nicotinic acid benzyl ester → 2-(3-Methoxycarbonyl-phenoxy)-nicotinic acid

HRID 843990Notes

Reaction equation

HRID 843990 reaction equation
C([O:8][C:9](=[O:27])[C:10]1[CH:15]=[CH:14][CH:13]=[N:12][C:11]=1[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([O:25][CH3:26])=[O:24])[CH:18]=1)C1C=CC=CC=1.[H][H]>CO.C(OCC)(=O)C.[Pd]>[CH3:26][O:25][C:23]([C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[O:16][C:11]1[N:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:9]([OH:27])=[O:8])=[O:24]

Participants

6

Reactant 2

HCID 544332282-(3-Methoxycarbonyl-phenoxy)-nicotinic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 226122032-(3-Methoxycarbonyl-phenoxy)-nicotinic acidYield 76.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution 2-(3-Methoxycarbonyl-phenoxy)-nicotinic acid benzyl ester (1.1 g) in methanol (15 ml) and ethyl acetate (15 ml) was added 10% palladium on carbon (0.2 g). This was shaken under 30 psi hydrogen for 2 hours. The catalyst was removed by filtration, and the solution was concentrated to give a solid which was triturated in methylene chloride/hexane to give a white solid (0.630 g). MW 273.26; MS (m/e) 274 (M++1).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe solution was concentrated
  3. customto give a solid which
  4. customwas triturated in methylene chloride/hexane

Sources & evidence

ORD record
ord-e91da9f62b7b48d4ab89f649f5e95118
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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