Dimethylformamide → Methyl ((1,3-dioxo-1,3-dihydro-2H-isoindol-2-YL)oxy)acetate

HRID 465248Notes

Reaction equation

HRID 465248 reaction equation
CN(C)C=O.[OH:6][N:7]1[C:11](=[O:12])[C:10]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]2[C:8]1=[O:17].Br[CH2:19][C:20]([O:22][CH3:23])=[O:21].C(=O)([O-])[O-].[K+].[K+]>O>[CH3:23][O:22][C:20]([CH2:19][O:6][N:7]1[C:8](=[O:17])[C:9]2=[CH:16][CH:15]=[CH:14][CH:13]=[C:10]2[C:11]1=[O:12])=[O:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10665N-HydroxyphthalimideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Product 1

HCID 748410Methyl ((1,3-dioxo-1,3-dihydro-2H-isoindol-2-YL)oxy)acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 50 ml of dry N,N-dimethylformamide are added 10 g of N-hydroxyphthalimide and 9.38 g of methyl bromoacetate, followed by addition of 8.5 g of potassium carbonate. The mixture is stirred at room temperature for 2 days and, then, poured into 400 ml of water. The resulting crystalline precipitate is recovered by filtration, washed with water, hexane and ether in this order to give colorless needles of N-methoxycarbonylmethyloxyphthalimide, m.p. 137°-142° C.

Workup

  1. filtrationThe resulting crystalline precipitate is recovered by filtration
  2. washwashed with water, hexane and ether in this order

Sources & evidence

ORD record
ord-ed695aba87e54b5bbcbf4d6b2ac42df8
Source dataset
uspto-grants-1985_10
Patent number
US04550105

Reaction notes

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