Ammonium Hydroxide → 1,3(2H,4H)-isoquinolinedione

HRID 1791285Notes

Reaction equation

HRID 1791285 reaction equation
[C:1]([CH2:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7](O)=[O:8])(O)=[O:2].[NH4+:14].[OH-]>>[C:7]1(=[O:8])[C:6]2[C:5](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][C:1](=[O:2])[NH:14]1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 66643Homophthalic acid

Product 1

HCID 3494351,3(2H,4H)-isoquinolinedioneYield 74%

Conditions

Temperature
200 °C

Procedure

2-(Carboxymethyl)benzoic acid (10 g, 55.6 mmol) was dissolved in concentrated NH4OH (15 mL) and then was evaporated to dryness under reduced pressure. The process was repeated with additional NH4OH (5 mL). The resulting residue was treated with 1,2-dichlorobenzene (20 mL) and heated with stirring at 200° C. without a condenser allowing the solvent to evaporate. The concentrated mixture was allowed to cool to room temperature, diluted with methanol (20 mL), and allowed to stand overnight. The precipitate was collected by filtration, washed with methanol, and dried under reduced pressure to provide the title compound as tan needles (6.6 g, 74%).

Workup

  1. customwas evaporated to dryness under reduced pressure
  2. additionThe resulting residue was treated with 1,2-dichlorobenzene (20 mL)
  3. temperatureheated
  4. customto evaporate
  5. temperatureto cool to room temperature
  6. additiondiluted with methanol (20 mL)
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with methanol
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-ac589d79f7aa450e9af1dc8575d8944e
Source dataset
uspto-grants-2006_07
Patent number
US07074805B2

Reaction notes

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