Isopropanol → 2-(4-Chloro-butyl)-isoindole-1,3-dione

HRID 5275

Reaction equation

HRID 5275 reaction equation
C(O)(C)C.[ClH:5].CNOC.Br[CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25].C(=O)(O)[O-].[Na+]>C(N(CC)CC)C>[Cl:5][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 93575N-(4-Bromobutyl)phthalimideHCID 516892Sodium Bicarbonate

Product 1

HCID 5949312-(4-Chloro-butyl)-isoindole-1,3-dioneYield 42.7%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a suspension of 50 ml of isopropanol containing N,O-dimethylhydroxylamine hydrochloride (3.97 g, 40.0 mmol) was added dropwise 5.56 ml of triethylamine. The resulting mixture became homogeneous after 5 minutes. There were added 2.00 g (7.09 mmol) of N-(4-bromobutyl)phthalimide and the mixture was refluxed for 58 hours. This was cooled to room temperature, then poured into 200 ml of saturated aqueous solution of sodium bicarbonate and extracted with chloroform. The organic layer was separated, was washed with water and dried over magnesium sulfate. Chloroform was distilled off and the residue was purified by column chromatography on silica gel. Development with 30% hexane-chloroform resulted in elution of 0.719 g of N-(4-chlorobutyl)-phthalimide and further development with chloroform resulted in 0.964 g (yield: 41%) of N-[4-(N-methoxy-N-methylamino)-butyl]phthalimide as an oil.

Workup

  1. temperaturethe mixture was refluxed for 58 hours
  2. extractionextracted with chloroform
  3. customThe organic layer was separated
  4. washwas washed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationChloroform was distilled off
  7. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c4193453fc9d45de86f939592e52320a
Source dataset
uspto-grants-1993_09
Patent number
US05244487

Linked notes

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