3-Aminophenol → 3-(6-Chloro-3-pyridazinyloxy)phenylamine

HRID 67160Notes

Reaction equation

HRID 67160 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[N:5]=[N:6][C:7](Cl)=[CH:8][CH:9]=1.[NH2:11][C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1>CS(C)=O>[Cl:3][C:4]1[N:5]=[N:6][C:7]([O:18][C:14]2[CH:13]=[C:12]([NH2:11])[CH:17]=[CH:16][CH:15]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 115683-AminophenolHCID 14798Sodium HydroxideHCID 673313,6-Dichloropyridazine

Product 1

HCID 130525673-(6-Chloro-3-pyridazinyloxy)phenylamine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A concentrated aqueous solution of 44 g of sodium hydroxide was added to a stirred solution of 149 g of 3,6-dichloropyridazine and 114.5 g of meta-aminophenol in 500 ml of dimethyl sulfoxide, at room temperature. The stirred mixture was heated, refluxed (150°-155° C.) for two hours, cooled, and filtered. The filter cake was recrystallized from aqueous methanol to give 3-(6-chloro-3-pyridazinyloxy)benzeneamine (1A), as an off-white solid, mp: 76°-77° C.

Workup

  1. temperatureThe stirred mixture was heated
  2. temperaturerefluxed (150°-155° C.) for two hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customThe filter cake was recrystallized from aqueous methanol

Sources & evidence

ORD record
ord-ab1e69a037ec42fda16e5eb79f4ada4d
Source dataset
uspto-grants-1982_08
Patent number
US04345077

Reaction notes

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