1-Chloromethylnaphthalene → 2-(naphthalen-1-ylmethyl)-1h-isoindole-1,3(2h)-dione

HRID 1726518Notes

Reaction equation

HRID 1726518 reaction equation
Cl[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[K].[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12>CN(C=O)C>[C:3]1([CH2:2][N:18]2[C:14](=[O:24])[C:15]3[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:17]2=[O:19])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 68451-ChloromethylnaphthaleneHCID 24194345Phthalimide potassium salt

Product 1

HCID 2280542-(naphthalen-1-ylmethyl)-1h-isoindole-1,3(2h)-dioneYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-chloromethyl-naphthalene (8.83 g, 50 mmol) in DMF (90 mL) was added phthalimide potassium salt (11.1 g, 60 mmol). The resultant solution was stirred at 100° C. overnight. The mixture was poured into ice-cold water and the precipitate was collected, washed with small amount of methanol and dried under vacuo to give 2-naphthalen-1-ylmethyl-isoindole-1,3-dione 52 (14.2 g, 99% yield). This material was used without further purification.

Workup

  1. additionThe mixture was poured into ice-cold water
  2. customthe precipitate was collected
  3. washwashed with small amount of methanol
  4. customdried under vacuo

Sources & evidence

ORD record
ord-32bdbc12b29348da9a841f9d00d61156
Source dataset
uspto-grants-2009_02
Patent number
US07491827B2

Reaction notes

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