Methyl bromoacetate → Phthalimidine

HRID 1862086Notes

Reaction equation

HRID 1862086 reaction equation
O[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:11].BrCC(OC)=O>CN(C=O)C>[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 2

HCID 60984Methyl bromoacetateHCID 115064794-Hydroxy-2,3-dihydroisoindol-1-one

Product 1

HCID 10199PhthalimidineYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxy 2,3-dihydro-1H-isoindol-1-one (27) (0.250 gm, 1.67 mmol) in DMF (5 ml) K2CO3 and was added, followed by addition of methyl bromoacetate, and the reaction mixture was stirred at room temperature for 2hr. Then the reaction mixture was then poured on ice and extracted with ethyl acetate (2×15 ml). After the standard workup, the residue was dissolved in methanol (3 ml), and treated with NaOH (5 ml, 1N) at 0° C. and then stirred for and additional hour. After the standard workup, the solid was recrystalized in methanol to give compound 29 (0.140 gm, 60%).

Workup

  1. additionThen the reaction mixture was then poured on ice
  2. extractionextracted with ethyl acetate (2×15 ml)
  3. dissolutionAfter the standard workup, the residue was dissolved in methanol (3 ml)
  4. additiontreated with NaOH (5 ml, 1N) at 0° C.
  5. stirringstirred for and additional hour
  6. customAfter the standard workup, the solid was recrystalized in methanol

Sources & evidence

ORD record
ord-2dfb53f5354e4c8b8ea2051047cfbc21
Source dataset
uspto-grants-2003_03
Patent number
US06534651B2

Reaction notes

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