Sodium Hydroxide → HCID 14998109, compound

HRID 1493365Notes

Reaction equation

HRID 1493365 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[OH-].[Na+].Cl[C:11]1[N:15]([CH3:16])[N:14]=[C:13]([CH3:17])[C:12]=1[CH:18]=[O:19]>CN(C)C=O>[CH3:16][N:15]1[C:11]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[C:12]([CH:18]=[O:19])[C:13]([CH3:17])=[N:14]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 27773975-Chloro-1,3-dimethylpyrazole-4-carboxaldehydeHCID 178516071HCID 178516071, compound

Product 1

HCID 14998109HCID 14998109, compoundYield 7.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

Under a nitrogen gas atmosphere, 3.0 g (0.032 mole) of 2-hydroxypyridine was added at 25° C. to 30 ml of a N,N-dimethylformamide solution containing 1.92 g (0.048 mole) of sodium hydroxide. Then, 5.1 g (0.032 mole) of 5-chloro-1,3-dimethyl-4-formylpyrazole in 20 ml of N,N-dimethylformamide was added to the mixture solution at 25° C. The reaction mixture was heated to 100° C. and stirred at 100° C. for 4 hours. The reaction mixture was then poured into 300 ml of ice water and extracted with two 100-ml portion of ethyl acetate. The organic layers were combined, washed once with 100 ml of saturated aqueous sodium chloride solution and dried over unhydrous magnesium sulfate, then concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel to obtain 0.55 g of 1,3-dimethyl- 5-(2-pyridyloxy)-4-formylpyrazole.

Workup

  1. extractionextracted with two 100-ml portion of ethyl acetate
  2. washwashed once with 100 ml of saturated aqueous sodium chloride solution
  3. dry with materialdried over unhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-44c701ed4389449eb8f2ed5f782fb645
Source dataset
uspto-grants-1991_06
Patent number
US05021446

Reaction notes

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