Hydrochloric Acid → Methyl 2-((1,3-dioxoisoindolin-2-yl)methyl)-3-oxobutanoate

HRID 10837Notes

Reaction equation

HRID 10837 reaction equation
N1CCC[CH:2]1[C:6](C)=[CH:7][C:8]([O:10][CH3:11])=[O:9].Br[CH2:14][N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25].Cl.[OH2:27]>CN(C)C=O>[C:19]1(=[O:20])[N:15]([CH2:14][CH:7]([C:6](=[O:27])[CH3:2])[C:8]([O:10][CH3:11])=[O:9])[C:16](=[O:25])[C:17]2=[CH:24][CH:23]=[CH:22][CH:21]=[C:18]12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 792441H-Isoindole-1,3(2H)-dione, 2-(bromomethyl)-HCID 69630084Methyl 3-tetrahydropyrrolyl-2-butenoate

Product 1

HCID 21982224Methyl 2-((1,3-dioxoisoindolin-2-yl)methyl)-3-oxobutanoateYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 3-tetrahydropyrrolyl-2-butenoate (29.0 g, 171.3 mmol) and N-(bromomethyl)phthalimide (43 g, 179.91 mmol) were dissolved in 250 ml of dimethylformamide, and the resulting mixture was then stirred at room temperature for 16 hours under a nitrogen atmosphere. After checking completion of the reaction with TLC, 1N HCl and water were added into the reaction mixture. The produced solid was filtered under a reduced pressure while washing with hexane and then recrystallized in 100% ethanol, thereby to obtain the desired product (32.26 g, 68%).

Workup

  1. additionwere added into the reaction mixture
  2. filtrationThe produced solid was filtered under a reduced pressure
  3. washwhile washing with hexane
  4. customrecrystallized in 100% ethanol

Sources & evidence

ORD record
ord-96ae0b4ef29e47f48fb533915a460abe
Source dataset
uspto-grants-2006_08
Patent number
US07094908B2

Reaction notes

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