Hydrochloric Acid → 2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzoic acid

HRID 1921091Notes

Reaction equation

HRID 1921091 reaction equation
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][O:2]1.[C:11]1(=[O:21])[NH:15][C:14](=[O:16])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12.[K].Cl>CN(C)C=O>[O:16]=[C:14]1[C:13]2[C:12](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11](=[O:21])[N:15]1[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=1[C:1]([OH:10])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6885PhthalideHCID 24194345Phthalimide potassium salt

Product 1

HCID 33132882-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzoic acidYield 71.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3H-isobenzofuran-1-one (18 g, 134 mmol) in dry N,N-dimethylformamide (110 mL) was added potassium phthalimide (27 g, 145 mmol). The mixture was stirred at reflux for 6 hours then cooled to 0° C. and treated with 1N hydrochloric acid (180 mL). The yellow solid thus formed was filtered, washed with water, with ethanol and dried in oven. Crystallization with ethanol afforded the title compound as white solid (27 g).

Workup

  1. temperatureat reflux for 6 hours
  2. customThe yellow solid thus formed
  3. filtrationwas filtered
  4. washwashed with water, with ethanol
  5. customdried in oven
  6. customCrystallization with ethanol

Sources & evidence

ORD record
ord-a894d82f4d2f4f0485291b8e64fac255
Source dataset
uspto-grants-2012_05
Patent number
US08173659B2

Reaction notes

Loading…