Sodium hydride → HCID 89579319, compound

HRID 714769Notes

Reaction equation

HRID 714769 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]#[N:9])[CH:2]=1.[H-].[Na+].Cl[C:13]1[N:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=1>CN(C)C=O>[CH3:20][O:19][C:16]1[N:15]=[N:14][C:13]([CH:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[C:8]#[N:9])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 744033-Chloro-6-methoxypyridazineHCID 809233-Pyridineacetonitrile

Product 1

HCID 89579319HCID 89579319, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-4 °C

Procedure

Pyridin-3-ylacetonitrile (14.3 g, 0.119 mol) were dissolved in dimethylformamide (300 ml) at 21° C. under a nitrogen atmosphere. The solution was cooled to −4° C., and sodium hydride (60% suspension in paraffin oil, 9.96 g, 0.249 mol) was added in portions. The resultant brown suspension was stirred at 0° C. for 45 minutes, and 3-chloro-6-methoxypyridazine (34.47 g, 0.231 mol) was subsequently added. The mixture was heated to 70° C. and stirred for 3 hours. After cooling, conventional work-up gave 18.6 g (68% yield) of (6-methoxypyridazin-3-yl)pyridin-3-ylacetonitrile;

Workup

  1. temperatureThe mixture was heated to 70° C.
  2. stirringstirred for 3 hours
  3. temperatureAfter cooling

Sources & evidence

ORD record
ord-677c133394c844ec893f19f8eb3181c8
Source dataset
uspto-grants-2015_11
Patent number
US09187469B2

Reaction notes

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