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

HRID 621139
Notes
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Reaction equation

HRID 621139 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 962Water
Solvent

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-604c7399b9774495add2b98c285848dc
Source dataset
uspto-grants-1989_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04822788

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes