Hydrochloric Acid → 4-[(6-Chloropyridazin-3-yl)oxy]aniline

HRID 67158

Reaction equation

HRID 67158 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6](Cl)[CH:5]=1.[Cl:12][C:13]1[N:14]=[N:15][C:16](Cl)=[CH:17][CH:18]=1.Cl>CS(C)=O>[Cl:12][C:13]1[N:14]=[N:15][C:16]([O:10][C:7]2[CH:8]=[CH:9][C:4]([NH2:3])=[CH:5][CH:6]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 673313,6-DichloropyridazineHCID 775784-Amino-2-chlorophenol

Product 1

HCID 106805234-[(6-Chloropyridazin-3-yl)oxy]aniline

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

12 g of sodium hydride was added in portions to a stirred solution of 71.8 g of 1A and 25 g of 3,6-dichloropyridazine in 300 ml of dimethyl sulfoxide, the temperature of the mixture being held at 50° C. The mixture then was stirred for one hour and poured into ice water. The mixture was slightly acidified with dilute hydrochloric acid, and was extracted with methylene chloride. The extract was washed with water, dried (magnesium sulfate) and the solvent was evaporated to give 4-(6-chloro-3-pyridazinyloxy)benzeneamine (1B), as a tan solid, mp: 126°-129° C.

Workup

  1. custombeing held at 50° C
  2. extractionwas extracted with methylene chloride
  3. washThe extract was washed with water
  4. dry with materialdried (magnesium sulfate)
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-3c0a74c576584da0a7ede398eec0b46b
Source dataset
uspto-grants-1982_08
Patent number
US04345076

Linked notes

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