4-AMINOISOINDOLIN-1-ONE → Phthalimidine

HRID 1070543Notes

Reaction equation

HRID 1070543 reaction equation
N[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:11]>C(OCC)(=O)C.C([O-])(O)=O.[Na+]>[C:6]1(=[O:11])[C:7]2[C:3](=[CH:2][CH:10]=[CH:9][CH:8]=2)[CH2:4][NH:5]1

Participants

4

Reactant 1

HCID 98555134-AMINOISOINDOLIN-1-ONE

Product 1

HCID 10199Phthalimidine

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A suspension of 2,3-dihydro-1H-isoindol-1-one 4 (7 gm, 0.04 mol.) in ethyl acetate and aq. NaHCO3 solution, was treated with mono-methyloctadioic acid chloride at room temperature. The reaction mixture was stirred at room temperature for 30 min. The solid that separated was filtered and dried under vacuum to give 2,3-dihydro-1H-isoindol-1-one 85, which was hydrolyzed by KOH (5 eq) in ethanol at 0° C. to generate acid 59 (5.775 gm).

Workup

  1. customThe solid that separated
  2. filtrationwas filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-cdaf8c55d051462ca589ac8135ee2876
Source dataset
uspto-grants-2005_06
Patent number
US06903079B2

Reaction notes

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