Sodium Hydroxide → 2-Hydroxy-5-methyl-1H-isoindole-1,3(2H)-dione

HRID 442603Notes

Reaction equation

HRID 442603 reaction equation
Cl.[NH2:2][OH:3].[OH-].[Na+].[CH3:6][C:7]1[CH:8]=[C:9]2[C:14](=O)[O:13][C:11](=[O:12])[C:10]2=[CH:16][CH:17]=1>O>[CH3:6][C:7]1[CH:8]=[C:9]2[C:14](=[O:13])[N:2]([OH:3])[C:11](=[O:12])[C:10]2=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 880694-Methylphthalic anhydrideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 158932232-Hydroxy-5-methyl-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Hydroxylamine hydrochloride in an amount of 21.4 g was dissolved in 80 ml of distilled water. To this solution, 12.3 g of NaOH dissolved in 50 ml of distilled water was added over a period of 30 minutes as the solution was cooled in an ice bath. Thereto, 50.0 g of 4-methylphthalic anhydride was further added, and stirred for 1 hour at room temperature, followed by 4-hour reflux. The reaction solution was cooled in an ice bath, and the powdery matter thus precipitated was filtered off and washed with water. The resultant crude crystals were recrystallized from an acetone/water mixture to give 27.0 g of 4-methyl-N-hydroxyphthalimide.

Workup

  1. additionwas added over a period of 30 minutes as the solution
  2. temperaturewas cooled in an ice bath
  3. waitfollowed by 4-hour
  4. temperaturereflux
  5. temperatureThe reaction solution was cooled in an ice bath
  6. customthe powdery matter thus precipitated
  7. filtrationwas filtered off
  8. washwashed with water
  9. customThe resultant crude crystals were recrystallized from an acetone/water mixture

Sources & evidence

ORD record
ord-26de291819484918b943e29cabdcb3c3
Source dataset
uspto-grants-1999_04
Patent number
US05891603

Reaction notes

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