P-Phenylenediamine → HCID 178507738, compound

HRID 2236921Notes

Reaction equation

HRID 2236921 reaction equation
CO[CH:3]=[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[NH:6][C:5]1=[O:15].[C:16]1([NH2:23])[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1>CN(C)C=O>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([NH:23][CH:3]=[C:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:14])[NH:6][C:5]2=[O:15])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 7814P-PhenylenediamineHCID 686923374-Methoxymethylene-4H-isoquinoline-1,3-dione

Product 1

HCID 178507738HCID 178507738, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

To a suspension of 4-Methoxymethylene-4H-isoquinoline-1,3-dione (203 mg, 1.0 mmol) in N,N-dimethylformamide (2.5 mL) is added 1,4-phenylenediamine (108 mg, 1.0 mmol). The reaction mixture is shaken at 115° C. for 1.5 hours. Upon cooling to ambient temperature, product precipitated out of solution. The product is recovered by filtration, rinsing with diethyl ether, and drying to yield 205.9 mg 4-[(4-Amino-phenylamino)-methylene]-4H-isoquinoline-1,3-dione.

Workup

  1. temperatureUpon cooling to ambient temperature
  2. customproduct precipitated out of solution
  3. filtrationThe product is recovered by filtration
  4. washrinsing with diethyl ether
  5. customdrying

Sources & evidence

ORD record
ord-ae74c5a41a474a1b8452724abb3ca93b
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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