Water → 2-(7-Hydroxyheptyl)isoindoline-1,3-dione

HRID 1911497Notes

Reaction equation

HRID 1911497 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].[C:10](=[NH:21])([O-:20])[C:11]1[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:13](=N)[O-:14].[K+].[K+].O.C(Cl)Cl>CN(C=O)C>[OH:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:21]1[C:10](=[O:20])[C:11]2[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:13]1=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 662841-Heptanol, 7-bromo-HCID 86762179HCID 86762179, compound

Product 1

HCID 189709042-(7-Hydroxyheptyl)isoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

585 mg of 7-bromoheptanol was dissolved in 5 mL of DMF. 833 mg of potassium phthalimidate was added, and the mixture was stirred for 4 h. 50 mL of water and 50 mL of DCM were added to the reaction system, which was violently vibrated and then isolated. The water layer was once again extracted with 50 mL of DCM. The two organic layers were combined, successively washed with 100 mL of water and 100 mL of saturated sodium chloride aqueous solution, dried over 5 g of anh. MgSO4 for 30 min, and concentrated via a rotary evaporator to obtain a pale yellow transparent oily liquid.

Workup

  1. customisolated
  2. extractionThe water layer was once again extracted with 50 mL of DCM
  3. washsuccessively washed with 100 mL of water and 100 mL of saturated sodium chloride aqueous solution
  4. dry with materialdried over 5 g of anh. MgSO4 for 30 min
  5. concentrationconcentrated via a rotary evaporator
  6. customto obtain a pale yellow transparent oily liquid

Sources & evidence

ORD record
ord-5a3cdb369ff64d53b4918e28170bd089
Source dataset
uspto-grants-2013_12
Patent number
US08604065B2

Reaction notes

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