1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → 4-(2-Phthalimidoethyloxy)pyridine

HRID 274691Notes

Reaction equation

HRID 274691 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.Br[CH2:9][CH2:10][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].C1CCN2C(=NCCC2)CC1>CN(C=O)C>[C:12]1(=[O:21])[N:11]([CH2:10][CH2:9][O:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]12

Participants

5

Reactant 3

HCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178418642HCID 178418642, compound

Product 1

HCID 190792114-(2-Phthalimidoethyloxy)pyridineYield 3.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4.76 g (50 mmol) of 4-hydroxypyridine and 13.97 g (55 mmol) of N-(2-bromoethyl)phthalimide in 80 ml of DMF, 8.23 ml (55 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added. The mixture was stirred at room temperature for 32 hours. After the solvent was distilled off, the mixture was poured into water and extracted with ethyl acetate. The mixture was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was distilled off. The residue was purified by-column chromatography (eluent: ethyl acetate) to obtain 0.41 g of the desired compound (yield: 3.1%, colorless crystal).

Workup

  1. distillationAfter the solvent was distilled off
  2. additionthe mixture was poured into water
  3. extractionextracted with ethyl acetate
  4. washThe mixture was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by-column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-ade200c334424e03bcafaf1b365d2052
Source dataset
uspto-grants-1995_02
Patent number
US05389658

Reaction notes

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