Sodium Hydroxide → HCID 58508774, compound

HRID 454745Notes

Reaction equation

HRID 454745 reaction equation
[OH-].[Na+].[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[C:10]([NH:18][C:19]([C:21]2[CH:22]=[N:23][CH:24]=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:26]=2)=[O:20])[CH:9]=1>O1CCOCC1>[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[C:10]([NH:18][C:19]([C:21]2[CH:22]=[N:23][CH:24]=[C:25]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:26]=2)=[O:20])[CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 58508783HCID 58508783, compound

Product 1

HCID 58508774HCID 58508774, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 2 mol/L aqueous solution of sodium hydroxide (0.19 mL) was added to a dioxane (3.0 mL) suspension of the obtained methyl 4-(furan-2-yl)-2-(5-phenylpyridine-3-carboxamido)benzoate (76 mg) at room temperature, followed by stirring at the same temperature for 3 hours and 20 minutes. A 2 mol/L aqueous solution of sodium hydroxide (0.19 mL) was added to the reaction mixture at room temperature, followed by stirring at 50 to 55° C. for 4 hours. After cooling the reaction mixture to room temperature, the solvent was evaporated under reduced pressure. To the obtained residue, 1 mol/L hydrochloric acid (1.5 mL) was added. The solid substance was collected by filtration to obtain 69 mg of 4-(furan-2-yl)-2-(5-phenylpyridine-3-carboxamido)benzoic acid as a white solid.

Workup

  1. stirringby stirring at 50 to 55° C. for 4 hours
  2. customthe solvent was evaporated under reduced pressure
  3. additionTo the obtained residue, 1 mol/L hydrochloric acid (1.5 mL) was added
  4. filtrationThe solid substance was collected by filtration

Sources & evidence

ORD record
ord-6ac200e5dc9a401187244ca3207b47af
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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