Phthalaldehyde → HCID 68443776, compound

HRID 1971321Notes

Reaction equation

HRID 1971321 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[CH2:5][CH:6]([NH2:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:15]1([CH:23]=O)[C:16]([CH:21]=[O:22])=[CH:17][CH:18]=[CH:19][CH:20]=1>ClCCl>[CH3:2][O:3][C:4](=[O:14])[CH2:5][CH:6]([N:13]1[CH2:23][C:15]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:21]1=[O:22])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 4807PhthalaldehydeHCID 2834577Methyl 3-phenyl-3-amino-propionate hydrochloride

Product 1

HCID 68443776HCID 68443776, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Amino-3-phenyl-propionic acid methyl ester hydrochloride (1.3 mmol, 1 eq), benzene-1,2-dicarbaldehyde (0.8 eq) and glacial acid (15 eq) are dissolved in dichloromethane and refluxed for 2 h (J. Chem. Soc., Chem Commun 1985, 1183). The mixture is concentrated in vacuo and partitioned between dichloromethane and water. The organic phase is dried over Na2SO4, filtered and concentrated in vacuo. 3-(1-Oxo-1,3-dihydro-isoindole-2-yl)-3-phenyl-propionic acid methyl ester is obtained as a brown solid (83% yield); ES-MS (MH+)=296.2; 1H-NMR (DMSO-d6, 400 MHz): δ [ppm] 7.73-7.30 (m, 9H), 5.82-5.78 (m, 1H), 4.54 (d, 1H, 17.4 Hz), 4.14 (d, 1H, 17.4 Hz), 3.57 (s, 3H), 3.31-3.28 (m, 2H).

Workup

  1. temperaturerefluxed for 2 h (J. Chem. Soc., Chem Commun 1985, 1183)
  2. concentrationThe mixture is concentrated in vacuo
  3. custompartitioned between dichloromethane and water
  4. dry with materialThe organic phase is dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e2c4f27851db40e0b5b987284ea0b43f
Source dataset
uspto-grants-2013_04
Patent number
US08431602B2

Reaction notes

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