Dimethylformamide → 2-(cyclopentyloxy)-1H-isoindole-1,3(2H)-dione

HRID 461971Notes

Reaction equation

HRID 461971 reaction equation
Br[CH:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1.[OH:7][N:8]1[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2[C:9]1=[O:18].C(N(CC)CC)C.CN(C)C=O>O>[CH:2]1([O:7][N:8]2[C:9](=[O:18])[C:10]3=[CH:17][CH:16]=[CH:15][CH:14]=[C:11]3[C:12]2=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 8728BromocyclopentaneHCID 10665N-Hydroxyphthalimide

Product 1

HCID 102632872-(cyclopentyloxy)-1H-isoindole-1,3(2H)-dioneYield 49.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of bromocyclopentane (14.9 g), N-hydroxyphthalimide (16.3 g), triethylamine (15 ml), and dimethylformamide (30 ml) was stirred for 16 hours, then poured into water (500 ml). The oily mixture was extracted with ethyl acetate, and the combined extracts, after washing (water), drying, and removal of solvent gave a while solid. This solid was recrystallised from ethanol to give N-cyclopentyloxyphthalimide (11.37 g, 49%); m.p. 81.2°-82.5°; λmax. (CHBr3) include 1780, 1720 cm-1 (CO--N--CO), 970 cm-1 ##STR72## τ values (DMSO-d6) 2.08 (4 Ar-H), 5.12 (cyclopentyl 1-H), 8.18 (4-CH2).

Workup

  1. extractionThe oily mixture was extracted with ethyl acetate
  2. washthe combined extracts, after washing (water)
  3. customdrying
  4. customremoval of solvent
  5. customgave a while solid
  6. customThis solid was recrystallised from ethanol

Sources & evidence

ORD record
ord-dbde6400f3b04929a5dda908a96eaddf
Source dataset
uspto-grants-1977_12
Patent number
US04064346

Reaction notes

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