Citric Acid → HCID 17962030, compound

HRID 349527Notes

Reaction equation

HRID 349527 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:5]([CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])[CH:4]=[N:3]1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[CH3:1][N:2]1[C:6]([NH:7][C:8]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[C:5]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 17962032HCID 17962032, compound

Product 1

HCID 17962030HCID 17962030, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 3-(1-methyl-5-triphenylmethylaminopyrazol-4-yl)propionate (22 g, 50 mmol) in methanol (60 ml) was added 10% aqueous sodium hydroxide solution (60 ml), and the mixture was stirred under reflux for 2 hours. The reaction mixture was acidified with 10% aqueous citric acid solution, and the mixture was extracted with a mixed solvent of chloroform and methanol. The extract was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was triturated with diisopropyl ether and dried in vacuo to give 3-(1-methyl-5-triphenylmethylaminopyrazol-4-yl)propionic acid (16 g) as a colorless solid.

Workup

  1. temperatureunder reflux for 2 hours
  2. extractionthe mixture was extracted with a mixed solvent of chloroform and methanol
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with diisopropyl ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-e4da183f9e5e4f71800198990a1d0d22
Source dataset
uspto-grants-2007_02
Patent number
US07179801B2

Reaction notes

Loading…