Sodium Carbonate → (1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)(phenyl)acetic acid

HRID 1417360Notes

Reaction equation

HRID 1417360 reaction equation
[C:1]1(NCC(O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12](=[O:15])([O-])[O-:13].[Na+].[Na+].[C:18]([N:23]1[C:27](=O)[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]2[C:24]1=[O:33])(OCC)=[O:19]>O>[C:18]1(=[O:19])[N:23]([CH:27]([C:26]2[CH:25]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:12]([OH:13])=[O:15])[C:24](=[O:33])[C:1]2=[CH:2][CH:3]=[CH:4][CH:5]=[C:6]12

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 66025N-Phenylglycine

Product 1

HCID 272803(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)(phenyl)acetic acidYield 51.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of phenylglycine (3.0 g, 20 mmoL) and sodium carbonate (2.23 g, 21 mmoL) in 450 mL of water is added N-carbethoxyphthalimide (4.38 g, 20 mmoL). After 45 minutes, the reaction slurry is filtered. The filtrate is stirred and the pH adjusted to 1-2 with 4N hydrochloric acid. After 1 hour, the resulting slurry is filtered and the solid washed with water. The solid is dried in vacuo (60° C., <1 mm) to afford 2.88 g (51%) of α-phthalimidophenylacetic acid, which can be alternatively named as N-phthaloylphenylglycine, as a white powder.

Workup

  1. filtrationthe reaction slurry is filtered
  2. waitAfter 1 hour
  3. filtrationthe resulting slurry is filtered
  4. washthe solid washed with water
  5. customThe solid is dried in vacuo (60° C., <1 mm)

Sources & evidence

ORD record
ord-1403a7378eea489ebe31b429fb1c6416
Source dataset
uspto-grants-1999_03
Patent number
US05877200

Reaction notes

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