Ethanol → 2-(5-nitro-1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)acetic acid

HRID 356205Notes

Reaction equation

HRID 356205 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[O:10][C:8](=O)[C:7]2=[CH:13][CH:14]=1)([O-:3])=[O:2].[NH2:15][CH2:16][C:17]([OH:19])=[O:18].O.C(O)C>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:15]([CH2:16][C:17]([OH:19])=[O:18])[C:8](=[O:10])[C:7]2=[CH:13][CH:14]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 750GlycineHCID 962WaterHCID 2309764-Nitrophthalic acid anhydride

Product 1

HCID 2727372-(5-nitro-1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)acetic acidYield 77.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-nitrophthalic anhydride (9.66 g, 50 mmol) and glycine (3.75 g, 50 mmol) in N,N-dimethylformamide was stirred for 30 minutes at 140° C. The reaction mixture was poured into water (150 mL). Resulting precipitate was collected by filtration and washed with water, which was collected by filtration and washed with water, which was recrystallized from ethanol to give 9.69 g (yield 77%) of the titled compound, m.p. 195.5°-196.5° C. (ethanol).

Workup

  1. customResulting precipitate
  2. filtrationwas collected by filtration
  3. washwashed with water, which
  4. filtrationwas collected by filtration
  5. washwashed with water, which
  6. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-ed06d8906bb24b659f434a577ff56c6c
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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