1,3-Isobenzofurandione, 5-(acetyloxy)- → 5-Hydroxy-2-(4-pyridinylamino)isoindole-1,3-dione hydrochloride

HRID 612451

Reaction equation

HRID 612451 reaction equation
C([O:4][C:5]1[CH:15]=[C:9]2[C:10]([O:12][C:13](=[O:14])[C:8]2=[CH:7][CH:6]=1)=O)(=O)C.[ClH:16].[NH:17]([C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1)[NH2:18]>C(O)(=O)C>[ClH:16].[OH:4][C:5]1[CH:15]=[C:9]2[C:8](=[CH:7][CH:6]=1)[C:13](=[O:14])[N:18]([NH:17][C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1)[C:10]2=[O:12]

Participants

4

Reactant 2

HCID 6397461,3-Isobenzofurandione, 5-(acetyloxy)-HCID 223202584-Hydrazinylpyridine hydrochloride

Product 1

HCID 195952755-Hydroxy-2-(4-pyridinylamino)isoindole-1,3-dione hydrochlorideYield 56.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 5-acetoxyphthalic anhydride (3.03 g), 4-hydrazinopyridine hydrochloride (2.04 g) and glacial acetic acid (15 ml) was heated under reflux, under nitrogen, for 4 hrs, with stirring. The reaction mixture was cooled to ambient temperature, the precipitate was collected, washed with water and dried at 60° C. under vacuum overnight. Trituration with hot absolute ethanol gave 2.3 g (56%) of product, mp >260° C.

Workup

  1. temperatureunder reflux, under nitrogen, for 4 hrs
  2. customthe precipitate was collected
  3. washwashed with water
  4. customdried at 60° C. under vacuum overnight

Sources & evidence

ORD record
ord-0a5be771ed6a4193a0d31ffed8500167
Source dataset
uspto-grants-1999_12
Patent number
US06004977

Linked notes

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