Hydrochloric Acid → Phthalylglycine aldehyde

HRID 2263282Notes

Reaction equation

HRID 2263282 reaction equation
Cl.C([O:4][CH:5](OCC)[CH2:6][N:7]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]1=[O:17])C>CC(C)=O>[O:17]=[C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:15](=[O:16])[N:7]1[CH2:6][CH:5]=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 3152862-Phthalimidoacetaldehyde Diethyl Acetal

Product 1

HCID 76201Phthalylglycine aldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 6 N aqueous hydrochloric acid solution (20 ml) was added to a solution of 2-(2,2-diethoxyethyl)-1H-isoindol-1,3(2H)-dione (1.0 g, 3.80 mmol) in acetone (20 ml), the mixture was stirred at room temperature for 6 hours, and the solvent was distilled off under reduced pressure. A saturated sodium hydrogen carbonate aqueous solution was added to the residue, and the mixture was extracted with chloroform. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to give the desired product as an oil.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionA saturated sodium hydrogen carbonate aqueous solution was added to the residue
  3. extractionthe mixture was extracted with chloroform
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cac1e5ee95ed4d73986fe1899759692f
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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