Methyl bromoacetate → Phthalimidine

HRID 1070540Notes

Reaction equation

HRID 1070540 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 2 hr. 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-c636589f53ea435d90b0fe0c0937529a
Source dataset
uspto-grants-2005_06
Patent number
US06903079B2

Reaction notes

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