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

HRID 2248075Notes

Reaction equation

S(=O)(=O)(O)O.[C:6]1(=[O:20])[N:10]([CH2:11][C:12]([OH:14])=[O:13])[C:9](=[O:15])[C:8]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:7]12.[N+:21]([O-])([OH:23])=[O:22]>>[N+:21]([C:17]1[CH:16]=[C:8]2[C:9](=[O:15])[N:10]([CH2:11][C:12]([OH:14])=[O:13])[C:6](=[O:20])[C:7]2=[CH:19][CH:18]=1)([O-:23])=[O:22]

Participants

Reactant 3

HCID 944Nitric Acid

HCID 1118Sulfuric Acid

HCID 20825N-Phthaloylglycine

Product 1

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

Procedure

To a mixture of concentrated sulfuric acid (350 ml) and fuming nitric acid (d=1.52)(60 ml) was added 2-phthalimidoacetic acid (70 g) with stirring and under ice-cooling. The mixture was stirred for 1 hour under ice-cooling and for 2 hours at room temperature, and poured into ice-water (2 l). The resultant precipitate was collected by filtration and recrystallized from a mixture of water (2 l) and ethanol (1 l) to give the title compound (60 g) as light yellow sharp-pointed needles.

Workup

temperaturecooling
stirringThe mixture was stirred for 1 hour under ice-
filtrationThe resultant precipitate was collected by filtration
customrecrystallized from a mixture of water (2 l) and ethanol (1 l)

Sources & evidence

ORD record: ord-afae845002a54f1c81910f4d88e14a00
Source dataset: uspto-grants-1991_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05037976

Reaction notes

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