1H-Isoindole-1,3(2H)-dione, 2-(bromomethyl)- → 2-(Phthalimidomethyloxy)pyridine

HRID 964102Notes

Reaction equation

HRID 964102 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH2:9][N:10]1[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]2[C:11]1=[O:20]>C1C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[C:11]1(=[O:20])[N:10]([CH2:9][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]12

Participants

5

Reactant 2

HCID 792441H-Isoindole-1,3(2H)-dione, 2-(bromomethyl)-HCID 178516071HCID 178516071, compound

Product 1

HCID 190791522-(Phthalimidomethyloxy)pyridineYield 39.3%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

In 4 ml of benzene were suspended 0.095 g (1.0 mmol) of 2-hydroxypyridine and 0.14 g (0.5 mmol) of silver carbonate, N-bromomethylphthalimide [0.29 g (1.2 mmol)] was added at room temperature, and the mixture was stirred at 80° C. for 14 hours under heating. After cooling, the residue was filtered and the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate/hexane=10:1) to obtain powder. The powder was recrystallized from ethyl acetate to obtain 0.10 g of the desired compound (yield: 39.0%, colorless columns).

Workup

  1. additionwas added at room temperature
  2. temperatureunder heating
  3. temperatureAfter cooling
  4. filtrationthe residue was filtered
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent: ethyl acetate/hexane=10:1)
  7. customto obtain powder
  8. customThe powder was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0963a453584747558468c369c862f080
Source dataset
uspto-grants-1998_06
Patent number
US05767121

Reaction notes

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