M-Phenylenediamine → 4-(3-amino-phenylamino)-2H-phthalazin-1-one

HRID 584115Notes

Reaction equation

HRID 584115 reaction equation
[NH:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[NH:3]1.[C:12]1([NH2:19])[CH:17]=[CH:16][CH:15]=[C:14]([NH2:18])[CH:13]=1.O.NN>CCO>[NH2:18][C:14]1[CH:13]=[C:12]([NH:19][C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4](=[O:11])[NH:3][N:1]=2)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7935M-PhenylenediamineHCID 24654Hydrazine hydrate (1:1)HCID 1357423743-Imino-2,3-dihydroisoindol-1-one

Product 1

HCID 223430214-(3-amino-phenylamino)-2H-phthalazin-1-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

3-Imino-2,3-dihydro-isoindol-1-one (50 mg, 0.34 mmol) and benzene-1,3-diamine (110 mg, 0.102 mmol) were heated at 200° C. for 16 hrs. The resulting mixture was dissolved in EtOH (600 μL) and hydrazine hydrate (200 μL) was added. After heating for 2 hours at 80° C. the mixture was concentrated in vacuo and dissolved in 1500 μL DMSO and directly applied to preparative HPLC to afford 4-(3-amino-phenylamino)-2H-phthalazin-1-one.

Workup

  1. concentrationwas concentrated in vacuo
  2. dissolutiondissolved in 1500 μL DMSO

Sources & evidence

ORD record
ord-18f8a7d484aa4e14861ea6acab539ec2
Source dataset
uspto-grants-2005_08
Patent number
US06924284B2

Reaction notes

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