2-Phenylethanol → 3-Chloro-6-phenethyloxypyridazine

HRID 1186781Notes

Reaction equation

HRID 1186781 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[C:9]1([CH2:15][CH2:16][OH:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[H-].[Na+]>CN1CCCC1=O>[Cl:1][C:2]1[N:3]=[N:4][C:5]([O:17][CH2:16][CH2:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 60542-PhenylethanolHCID 24758Sodium hydrideHCID 673313,6-Dichloropyridazine

Product 1

HCID 431280563-Chloro-6-phenethyloxypyridazine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

3,6-Dichloropyridazine (1.0 g, 6.712 mmol), 2-phenylethanol (820 mg, 6.712 mmol) and sodium hydride (60 percent suspension in oil, 268 mg, 6.712 mmol) were stirred in 25 ml of N-methylpyrrolidin-2-one at room temperature for 30 minutes. After concentrating, water and ethyl acetate were added, and the organic phase was removed, concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 878 mg (56%), M+H+: 235.1.

Workup

  1. concentrationAfter concentrating
  2. additionwater and ethyl acetate were added
  3. customthe organic phase was removed
  4. concentrationconcentrated
  5. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-050a1149c3394e89821c411c6e8ed14e
Source dataset
uspto-grants-2014_03
Patent number
US08673917B2

Reaction notes

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