Citric Acid → HCID 58508566, compound

HRID 454565Notes

Reaction equation

HRID 454565 reaction equation
[OH-].[Na+:2].C([O:6][C:7]1[CH:30]=[CH:29][C:28]([C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)=[CH:27][C:8]=1[C:9]([NH:11][C:12]1[CH:21]=[C:20]([C:22]2[O:23][CH:24]=[CH:25][CH:26]=2)[CH:19]=[CH:18][C:13]=1[C:14]([O:16]C)=[O:15])=[O:10])(=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1>[O:23]1[CH:24]=[CH:25][CH:26]=[C:22]1[C:20]1[CH:19]=[CH:18][C:13]([C:14]([O-:16])=[O:15])=[C:12]([NH:11][C:9](=[O:10])[C:8]2[CH:27]=[C:28]([C:31]3[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=3)[CH:29]=[CH:30][C:7]=2[OH:6])[CH:21]=1.[Na+:2]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 66990695HCID 66990695, compound

Product 1

HCID 58508566HCID 58508566, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Dioxane (3 mL) and a 2 mol/L aqueous solution of sodium hydroxide (0.19 mL) were added to the obtained methyl 2-(2-acetoxy-5-(pyridin-3-yl)benzamido)-4-(furan-2-yl)benzoate (0.18 g), followed by stirring at room temperature for 3 hours and 10 minutes and then at 70° C. for 1 hour and 30 minutes. The reaction mixture was cooled to room temperature and adjusted to a pH of 6.0 with a 10% aqueous solution of citric acid. The solid substance was collected by filtration, and methanol (1.0 mL) and a 1 mol/L aqueous solution of sodium hydroxide (0.055 mL) were added thereto. The solid substance was collected by filtration to obtain 0.044 g of sodium 4-(furan-2-yl)-2-(2-hydroxy-5-(pyridin-3-yl)benzamido)benzoate as a white solid.

Workup

  1. waitat 70° C. for 1 hour
  2. custom30 minutes
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationThe solid substance was collected by filtration, and methanol (1.0 mL)
  5. additiona 1 mol/L aqueous solution of sodium hydroxide (0.055 mL) were added
  6. filtrationThe solid substance was collected by filtration

Sources & evidence

ORD record
ord-b58451b01e11423ebd52fcc2ad54c759
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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