Triethylamine → 2-(Pyridin-2-ylmethoxy)-isoindole-1.3-dione

HRID 375791Notes

Reaction equation

HRID 375791 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].Cl.[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20]Cl.C(N(CC)CC)C>C(#N)C>[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][O:1][N:2]1[C:3](=[O:12])[C:4]2[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 23392Picolyl chloride hydrochloride

Product 1

HCID 122139452-(Pyridin-2-ylmethoxy)-isoindole-1.3-dioneYield 73.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under anhydrous conditions (positive nitrogen pressure, presence of 3Å molecular sieves), a mixture of N-hydroxyphthalimide (10.0 g, 0.061 mole), 2-picolylchloride hydrochloride (10.0 g, 0.061 mole), and triethylamine (18.5 g, 0.183 mol) in 100 ml of anhydrous acetonitrile was refluxed for 6 hours. After overnight stirring at ambient temperature, TLC showed that the starting materials were practically consumed. The solvent was evaporated and the residue dissolved in 200 ml of EtOAc. The solution was washed with 1N NaOH (100 ml), water (2×200 ml), brine (1×200 m ml) and dried (MgSO4). After removal of the solvent, the crude product was recrystallized from EtOAc/hexane to afford 11.4 g (73.6%) of title product.

Workup

  1. temperaturewas refluxed for 6 hours
  2. customwere practically consumed
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in 200 ml of EtOAc
  5. washThe solution was washed with 1N NaOH (100 ml), water (2×200 ml), brine (1×200 m ml)
  6. dry with materialdried (MgSO4)
  7. customAfter removal of the solvent
  8. customthe crude product was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-85accd8a31f14845bd4731fa3add635c
Source dataset
uspto-grants-1996_01
Patent number
US05488054

Reaction notes

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