Hydrochloric Acid → Phthalylglycine aldehyde

HRID 2364333Notes

Reaction equation

HRID 2364333 reaction equation
C([O:3][CH:4](OCC)[CH2:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:16])C.Cl>C1COCC1>[O:16]=[C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14](=[O:15])[N:6]1[CH2:5][CH:4]=[O:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 3152862-Phthalimidoacetaldehyde Diethyl Acetal

Product 1

HCID 76201Phthalylglycine aldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[2,2-bis(ethyloxy)ethyl]-1H-isoindole-1,3(2H)-dione (24.60 g, 93 mmol) in THF (150 mL) under nitrogen was treated with 1N HCl (aq) (75 mL, 75 mmol) and brought to reflux. After stirring for 20 h, the reaction was evaporated in vacuo and the residue was triturated with 1N HCl (100 mL). The resulting solid was collected by filtration, washed with 1N HCl, water, and Et2O and dried under high vacuum to provide the desired product as a white solid: 1H NMR (d6-DMSO, 300 MHz) δ 9.60 (1H, s), 7.87-7.95 (4H, m), 4.6 (2H, s).

Workup

  1. temperatureto reflux
  2. customthe reaction was evaporated in vacuo
  3. customthe residue was triturated with 1N HCl (100 mL)
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with 1N HCl, water, and Et2O
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-e0c23933773546f1a395d9cfe1ad8b33
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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