Hydrochloric Acid → HCID 67045216, compound

HRID 1023692Notes

Reaction equation

HRID 1023692 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([N:23]([CH3:25])[CH3:24])[CH:20]=3)[C:15]2=[O:26])=[CH:10][CH:9]=1)C.[OH-].[Na+].Cl>C(O)C>[CH3:25][N:23]([CH3:24])[C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:26])[N:14]([C:11]1[CH:12]=[CH:13][C:8]([CH2:7][CH2:6][CH2:5][C:4]([OH:27])=[O:3])=[CH:9][CH:10]=1)[CH2:22]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67045130HCID 67045130, compound

Product 1

HCID 67045216HCID 67045216, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-[4-(5-dimethylamino-1-oxo-1,3-dihydro-isoindol-2-yl)-phenyl]-butyric acid ethyl ester (0.13 g, 0.35 mmol) obtained in Example 33 in ethanol (15 ml) was added with 0.5 M NaOH aq. (3.3 ml), and the mixture was stirred at room temperature for 10 hours. The reaction solution was made acidic by adding 10% hydrochloric acid, and then extracted with chloroform. The chloroform layer was washed with saturated brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=20:1) and recrystallization (ethanol) to obtain 4-[4-(5-dimethylamino-1-oxo-1,3-dihydro-isoindol-2-yl)-phenyl]-butyric acid (Compound 16) as a pale brown powdery substance (79.4 mg, yield: 66.7%).

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform layer was washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=20:1) and recrystallization (ethanol)

Sources & evidence

ORD record
ord-8b8d9b9325324629ba40b2b179d4a1b2
Source dataset
uspto-grants-2014_05
Patent number
US08722723B2

Reaction notes

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