N-Hydroxyphthalimide → HCID 22285910, compound

HRID 1062265Notes

Reaction equation

HRID 1062265 reaction equation
C(N(C(C)C)CC)(C)C.[OH:10][N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21].Br[CH2:23][CH2:24][CH2:25][OH:26]>CN(C)C=O.C(OCC)(=O)C>[OH:26][CH2:25][CH2:24][CH2:23][O:10][N:11]1[C:12](=[O:21])[C:13]2[C:14](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:16]

Participants

6

Reactant 3

HCID 10665N-HydroxyphthalimideHCID 123083-Bromo-1-propanolHCID 81531Diisopropylethylamine

Product 1

HCID 22285910HCID 22285910, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Diisopropylethylamine (43 mL, 246 mmol) was added to a stirring solution of N-hydroxyphthalimide (20.6 g, 123 mmol) in dimethylformamide (95 mL). After 5 minutes, 3-bromopropanol (11.5 mL, 127 mmol) was added and the reaction mixture was heated to 80° C. for 18 h. The cooled solution was diluted with ethyl acetate (700 mL) and was washed with water (4×500 mL) and saturated brine (2×500 mL), dried over sodium sulfate and concentrated to an oil that solidified on standing to afford 2-(3-hydroxy-propoxy)-isoindole-1,3-dione (17.5 g, 65% yield) as a tan-colored solid: 1H NMR (400 MHz, CDCl3) δ 7.81 (m, 2H), 7.74 (m, 2H), 4.36 (t, 2H, J=5.6 Hz), 3.92 (t, 2H, J=5.9 Hz), 1.98 (quintet, 2H, J=5.9 Hz).

Workup

  1. washwas washed with water (4×500 mL) and saturated brine (2×500 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to an oil that

Sources & evidence

ORD record
ord-1543cdc6de0f49a0880e6880f494549d
Source dataset
uspto-grants-2005_11
Patent number
US06960614B2

Reaction notes

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