Beta-Alanine → 3-Phthalimidopropionic acid

HRID 355537Notes

Reaction equation

HRID 355537 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].[C:7]1(=O)[O:12][C:10](=[O:11])[C:9]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:8]12.C(OCC)(=O)C>CCCCCC>[C:7]1(=[O:12])[N:1]([CH2:2][CH2:3][C:4]([OH:6])=[O:5])[C:10](=[O:11])[C:9]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:8]12

Participants

5

Reactant 3

HCID 239Beta-AlanineHCID 6811Phthalic AnhydrideHCID 8857Ethyl Acetate

Product 1

HCID 768593-Phthalimidopropionic acidYield 100.2%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of β-alanine (89 g) and phthalic anhydride (148 g) was heated at 180° C. to 190° C. for 30 min. The mixture was cooled to 60° C. and ethyl acetate (500 ml) was added, and the mixture was stirred at 0° C. for 1 hr. n-Hexane is added to the reaction mixture and the reactant crystals were collected filteration to afford 219.5 g of 3-phthalimidopropionic acid in colorless crystals.

Workup

  1. temperaturewas heated at 180° C. to 190° C. for 30 min
  2. customthe reactant crystals were collected filteration

Sources & evidence

ORD record
ord-773ca0c0a7ea44ecbb9ed437eec53451
Source dataset
uspto-grants-1998_11
Patent number
US05831091

Reaction notes

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