Hydrochloric Acid → 2-(2-Methoxyethoxy)-1H-isoindole-1,3(2H)-dione

HRID 1874080Notes

Reaction equation

HRID 1874080 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH3:21][O:22][CH2:23][CH2:24]Br.Cl>CN1C(=O)CCC1>[CH3:21][O:22][CH2:23][CH2:24][O:1][N:2]1[C:3](=[O:12])[C:4]2[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:7]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 10665N-HydroxyphthalimideHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl ether

Product 1

HCID 129191152-(2-Methoxyethoxy)-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of N-hydroxyphthalimide (30.0 g, 184 mmol) and potassium carbonate (25.4 g, 138 mmol) in 300 mL NMP is heated to 50° C. Potassium iodide (0.15 g, 0.90 mmol) and 2-bromoethyl methyl ether (19.0 ml, 202 mmol) are added and the reaction mixture is stirred at 80° C. for 2 h. The reaction mixture is poured on 1 M aqueous HCl and extracted with ethyl acetate. The combined organic phases are dried over MgSO4 and concentrated in vacuo. The residue is triturated with water and subsequently crystallized from EtOH. Yield: 17.1 g.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic phases are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue is triturated with water
  5. customsubsequently crystallized from EtOH

Sources & evidence

ORD record
ord-2c2257c05b0e42d6a8cca092a660c671
Source dataset
uspto-grants-2012_11
Patent number
US08304556B2

Reaction notes

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