Ethanol → HCID 178526329, compound

HRID 1174484Notes

Reaction equation

HRID 1174484 reaction equation
[C:1](#[N:10])[C:2]1[C:3](=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:4]#[N:5].[NH2:11][OH:12].CC[OH:15]>>[C:1]1(=[N:10][OH:15])[C:2]2[C:3](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[N:11][OH:12])[NH:5]1

Participants

4

Reactant 3

HCID 702EthanolHCID 787HydroxylamineHCID 7042Phthalonitrile

Product 1

HCID 178526329HCID 178526329, compoundYield 85.4%

Procedure

Phthalonitrile (1 g, 7.8 mmol) and hydroxylamine (1.9 cm3, 31.2 mmol, 4 eq) in EtOH (25 cm3) were stirred under reflux for 60 hours, after which the volatiles were removed under reduced pressure and the residue was washed with EtOH (2 cm3) and CH2Cl2 (2 cm3) to give the cyclised product isoindoline-1,3-dione dioxime (1.18 g, 85.4%) as a pale yellow solid, mp 272-275° C. (decomposed) (lit 271° C.).

Workup

  1. temperatureunder reflux for 60 hours
  2. customafter which the volatiles were removed under reduced pressure
  3. washthe residue was washed with EtOH (2 cm3) and CH2Cl2 (2 cm3)

Sources & evidence

ORD record
ord-8fd4642caf0c499c8fa70067a2f4b041
Source dataset
uspto-grants-2010_11
Patent number
US07838483B2

Reaction notes

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