2-Phthalimidoacetaldehyde Diethyl Acetal → Phthalylglycine aldehyde

HRID 1254333Notes

Reaction equation

HRID 1254333 reaction equation
C([O:3][CH:4](OCC)[CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16])C>C(O)=O>[O:16]=[C:7]1[C:8]2[C:9](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:11])[N:6]1[CH2:5][CH:4]=[O:3]

Participants

3

Reactant 1

HCID 3152862-Phthalimidoacetaldehyde Diethyl Acetal

Product 1

HCID 76201Phthalylglycine aldehydeYield 93.1%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Phthalimidoacetaldehyde diethyl acetal (76.40 g, 0.32 mol, Aldrich) was dissolved in 85% formic acid (300 mL) and stirred for 2 h at rt. After TLC analysis indicated full conversion to the aldehyde (Rf=0.34 1:1 hexanes/EtOAc, 2,4-DNP: yellow), the solvent was removed and the residue was dried under vacuum (150 mm Hg) to afford 2-(1,3-dioxoisoindolin-2-yl)acetaldehyde (56.34 g, 93%) as a white solid. 1H NMR: 4.57 (s, 2H), 7.76 (m, 2H), 7.77(m, 2H), 9.66 (s, 1H).

Workup

  1. customthe solvent was removed
  2. customthe residue was dried under vacuum (150 mm Hg)

Sources & evidence

ORD record
ord-84fe18d1e34a4c50901d6add733bb61e
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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