HCID 54363311, compound → HCID 22269716, compound

HRID 488495Notes

Reaction equation

HRID 488495 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=2)=[CH:13][CH:12]=1>C1COCC1.CCO.[OH-].[Na+]>[CH3:26][O:25][C:23]1[CH:24]=[C:19]([CH2:18][CH2:17][C:14]2[CH:15]=[CH:16][C:11]([NH:10][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:3]([OH:31])=[O:2])=[CH:12][CH:13]=2)[CH:20]=[C:21]([O:29][CH3:30])[C:22]=1[O:27][CH3:28]

Participants

4

Reactant 1

HCID 54363311HCID 54363311, compound

Product 1

HCID 22269716HCID 22269716, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of 2-{4-[2-(3,4,5-trimethoxyphenyl)ethyl]phenylamino}-benzoic acid methyl ester (0.62 g, 1.47 mmol) in THF-EtOH (2:1, 6 mL), 1N NaOH solution (4 mL) was added, and the reaction mixture was heated to reflux for 5 hours. The reaction mixture was then concentrated in vacuo to remove the organic solvent. The residue was acidified with concentrated HCl (pH 3). This precipitate was collected by filtration, triturated with boiling MeOH—H2O (4:1) and dried in vacuum at room temperature for 16 hours to give the title compound as a white solid, 0.59 g (1.45 mmol, 98.5%). mp 146.0-147.0° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 5 hours
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. customto remove the organic solvent
  5. filtrationThis precipitate was collected by filtration
  6. customtriturated with boiling MeOH—H2O (4:1)
  7. customdried in vacuum at room temperature for 16 hours

Sources & evidence

ORD record
ord-816a431998cb492cb5165003c0a765f9
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

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