Hydrochloric Acid → HCID 22269690, compound

HRID 488525Notes

Reaction equation

HRID 488525 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][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[CH:22][CH:21]=2)=[CH:13][CH:12]=1.[OH-].[K+].Cl>CCO.CC(C)=O>[CH2:29]([N:26]([CH2:27][CH3:28])[C:23]1[CH:22]=[CH:21][C:20]([CH2:19][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:25][CH:24]=1)[CH3:30]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 54220238HCID 54220238, compound

Product 1

HCID 22269690HCID 22269690, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

To an emulsion of 2-{4-[3-(4-diethylaminophenyl)propyl]phenylamino}-benzoic acid methyl ester (1.68 g, 4.03 mmol) in EtOH (50 mL) was added aqueous 3 M-KOH solution (4.0 mL, 12.0 mmol) at room temperature, then the mixture was allowed to heat under reflux for 40 minutes. The reaction mixture was cooled to room temperature and neutralized with aqueous 1.0 M-HCl solution to pH 9.0. The mixture was concentrated under reduced pressure to remove EtOH, and the resulting aqueous solution was extracted with CHCl3 (50 mL, 3 times). The combined extract was washed with brine (10 mL) and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and purification by column chromatography (silica gel 60N, conc NH4OH/MeOH/CHCl3 0.2:2:100 to 0.5:5:100) afforded a yellow oil. This oil was diluted with acetone, and the solution was concentrated under reduced pressure at room temperature to give the title compound as an amorphous solid (1.62 g, 99% for 0.2 hydrate).

Workup

  1. temperatureto heat
  2. temperatureunder reflux for 40 minutes
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customto remove EtOH
  5. extractionthe resulting aqueous solution was extracted with CHCl3 (50 mL, 3 times)
  6. extractionThe combined extract
  7. washwas washed with brine (10 mL)
  8. dry with materialdried over anhydrous Na2SO4
  9. customThe solvent was removed under reduced pressure and purification by column chromatography (silica gel 60N, conc NH4OH/MeOH/CHCl3 0.2:2:100 to 0.5:5:100)
  10. customafforded a yellow oil
  11. concentrationthe solution was concentrated under reduced pressure at room temperature

Sources & evidence

ORD record
ord-a2af741be0dc4b16beb43dd1750f4cbd
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

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