Triethylamine → 2-((4-Methoxybenzyl)oxy)isoindoline-1,3-dione

HRID 1584034Notes

Reaction equation

HRID 1584034 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].[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1.C(N(CC)CC)C>CN(C)C=O>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][O:1][N:2]2[C:3](=[O:12])[C:4]3=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]3[C:6]2=[O:7])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 1650214-Methoxybenzyl bromide

Product 1

HCID 7178912-((4-Methoxybenzyl)oxy)isoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-hydroxyphthalimide (11.1 g) and p-methoxybenzyl bromide (13.7 ml) in N,N-dimethylformamide (100 ml) is added triethylamine (6.8 g), and the mixture is stirred at room temperature for 1 hour and at 60° to 70° C. for 1 hour. The reaction mixture is poured into ice water and extracted with ethyl acetate. The extract solution is washed with diluted hydrochloric acid and water, dried and concentrated under reduced pressure. The residue is crystallized from methanol to give N-p-methoxybenzyloxyphthalimide (17 g). mp. 139°-141° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract solution is washed with diluted hydrochloric acid and water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is crystallized from methanol

Sources & evidence

ORD record
ord-8de6dc04807147e1963b25156eccbd71
Source dataset
uspto-grants-1985_11
Patent number
US04555578

Reaction notes

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