Ethanol → HCID 178526329, compound

HRID 2403111Notes

Reaction equation

HRID 2403111 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-0189a0b957224558bb71d3a95ea74ed5
Source dataset
uspto-grants-2014_08
Patent number
US08802609B2

Reaction notes

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