Ethanolamine → 2-[(6-Chloropyridazin-3-yl)oxy]ethan-1-amine--hydrogen chloride (1/1)

HRID 745502Notes

Reaction equation

HRID 745502 reaction equation
[H-].[Na+].[NH2:3][CH2:4][CH2:5][OH:6].[Cl:7][C:8]1[N:9]=[N:10][C:11](Cl)=[CH:12][CH:13]=1>C1C=CC=CC=1>[ClH:7].[NH2:3][CH2:4][CH2:5][O:6][C:11]1[N:10]=[N:9][C:8]([Cl:7])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 24758Sodium hydrideHCID 673313,6-Dichloropyridazine

Product 1

HCID 233135662-[(6-Chloropyridazin-3-yl)oxy]ethan-1-amine--hydrogen chloride (1/1)Yield 54.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a suspension of 4.2 g of 61% sodium hydride in 100 ml of benzene was added dropwise 6.2 g of 2-aminoethanol at room temperature. Then, 15 g of 3,6-dichloropyridazine was added, and the mixture was refluxed for 1 hour. After cooling, the reaction mixture was washed with water, and dried over magnesium sulfate. After evaporating the solvent, the residue was treated with hydrogen chrolide-ether solution to give 5.73 g of 3-(2-aminoethoxy)-6-chloropyridazine hydrochloride as crystals.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperatureAfter cooling
  3. washthe reaction mixture was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporating the solvent
  6. additionthe residue was treated with hydrogen chrolide-ether solution

Sources & evidence

ORD record
ord-5c6ef1edb3be4f9d8326bfb04e2e20ab
Source dataset
uspto-grants-1986_07
Patent number
US04599333

Reaction notes

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