Cyclopentylamine → 2-Cyclopentyl-5-hydroxyisoindoline-1,3-dione

HRID 404954Notes

Reaction equation

HRID 404954 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=O)[C:5]2=[CH:11][CH:12]=1.[CH:13]1([NH2:18])[CH2:17][CH2:16][CH2:15][CH2:14]1>C1(C)C=CC=CC=1>[CH:13]1([N:18]2[C:9](=[O:10])[C:4]3[C:5](=[CH:11][CH:12]=[C:2]([OH:1])[CH:3]=3)[C:6]2=[O:8])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 6397475-Hydroxy-1,3-dihydro-2-benzofuran-1,3-dione

Product 1

HCID 138973992-Cyclopentyl-5-hydroxyisoindoline-1,3-dioneYield 80.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Hydroxy-phthalic anhydride (5.4 g, 32.9 mmol), cyclopentyl amine (4.9 mL, 49.6 mmol) and 4 Å molecular sieves in toluene (136 mL) were stirred at reflux overnight. The reaction mixture was filtered and the solvent was evaporated in vacuo to obtain the product (6.1 g, 80%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6): δ 7.60 (d, J=7.8 Hz, 1H), 7.05-7.01 (m, 2H), 4.50-4.40 (m, 1H), 1.97-1.52 (m, 8H).

Workup

  1. temperatureat reflux overnight
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-6825de91ae264248b2c1d4cb7deb289a
Source dataset
uspto-grants-2014_06
Patent number
US08748632B2

Reaction notes

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