Chloroacetamide → 2-[(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]acetamide

HRID 1892314Notes

Reaction equation

HRID 1892314 reaction equation
[OH:1][N:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12].Cl[CH2:14][C:15]([NH2:17])=[O:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[O:12]=[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10](=[O:11])[N:2]1[O:1][CH2:14][C:15]([NH2:17])=[O:16]

Participants

5

Reactant 3

HCID 6580ChloroacetamideHCID 10665N-HydroxyphthalimideHCID 11430Potassium Carbonate

Product 1

HCID 140744182-[(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-hydroxyisoindoline-1,3-dione (2.4 g, 14.71 mmol), 2-chloroacetamide (1.65 g, 17.65 mmol) and K2CO3 (2.44 g, 17.65 mmol) in 40 mL of DMF was stirred at 90° C. overnight. The solid was removed by filtration and the solution was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with EtOAc/methanol gradient to afford the title compound. 1H-NMR (400 MHz, DMSO-d6) δ ppm 7.89 (dd, 1H), 7.68-7.64 (m, 2H), 7.45-7.43 (m, 2H), 7.35 (s, 1H), 4.23 (s, 2H). LCMS (method A): [MH]+=221, tR=2.665 min.

Workup

  1. customThe solid was removed by filtration
  2. concentrationthe solution was concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography on silica gel eluting with EtOAc/methanol gradient

Sources & evidence

ORD record
ord-1862622590ff44cb91490366099a199c
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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