O-Phenylenediamine → HCID 178515895, compound

HRID 499157Notes

Reaction equation

HRID 499157 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([C:8](O)=O)=[CH:4][CH:3]=1.[C:11]1([NH2:18])[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH2:17].C([O-])(O)=[O:20].[Na+]>O>[NH:17]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:18]=[C:8]1[C:5]1[N:6]=[N:7][C:2]([OH:20])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 516892Sodium BicarbonateHCID 64157626-chloropyridazine-3-carboxylic Acid

Product 1

HCID 178515895HCID 178515895, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 6-chloropyridazine-3-carboxylic acid (0.800 g, 5.060 mmol), o-phenylenediamine (0.550 g, 5.080 mmol) amd polyphosphoric acid (25 g) was heated at 150-170° C. with stirring for 3 hours. Water was added to the reaction mixture, and the resulting solution was neutralized with NaHCO3, and extracted with ethyl acetate. The organic phase was dried and evaporated to afford 6-(1H-benzoimidazol-2-yl)pyridazin-3-ol was isolated as a white solid in 31% yield (0.322 g, 1.570 mmol).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase was dried
  3. customevaporated

Sources & evidence

ORD record
ord-a0ca01f2158c4e49ae7a725daed7c602
Source dataset
uspto-grants-2010_08
Patent number
US07767677B2

Reaction notes

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