Methanol → HCID 53944487, compound

HRID 488524Notes

Reaction equation

HRID 488524 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]3[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=3[C:20]([OH:22])=[O:21])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.OS(O)(=O)=O.[CH3:32]O>>[CH3:32][O:21][C:20](=[O:22])[C:19]1[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=1[NH:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][CH2:8][C:5]2[CH:4]=[CH:3][C:2]([NH2:1])=[CH:7][CH:6]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 22269797HCID 22269797, compound

Product 1

HCID 53944487HCID 53944487, compound

Procedure

To a solution of 2-{4-[3-(4-aminophenyl)propyl]phenylamino}benzoic acid (Example 159) (2.34 g, 6.75 mmol) in MeOH (50 mL) was added concentrated H2SO4 (1.0 mL) at room temperature. The mixture was stirred under reflux for 3.0 days. The reaction was quenched with Et3N (10 mL) at 5° C., and the solvent was removed under reduced pressure. The residue was diluted with water (20 mL) and extracted with Et2O (20 mL, 4 times). The combined ether layer was washed with water (10 mL) and brine (10 mL), and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and purification by column chromatography afforded crude title compound as a yellow amorphous material (2.59 g). This material was used without further purification.

Workup

  1. temperatureunder reflux for 3.0 days
  2. customThe reaction was quenched with Et3N (10 mL) at 5° C.
  3. customthe solvent was removed under reduced pressure
  4. additionThe residue was diluted with water (20 mL)
  5. extractionextracted with Et2O (20 mL, 4 times)
  6. washThe combined ether layer was washed with water (10 mL) and brine (10 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. customThe solvent was removed under reduced pressure and purification by column chromatography

Sources & evidence

ORD record
ord-6ab4d245f9d5430a8b1b9a8ef9154797
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

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