Pyridine → 3,5-Dimethyl-1-phenyl-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 8059

Reaction equation

HRID 8059 reaction equation
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:9]([O:11][C:12](=[O:20])[CH:13]([C:17](=O)[CH3:18])[C:14](=O)[CH3:15])[CH3:10].N1C=CC=CC=1>C(O)C>[CH2:9]([O:11][C:12]([C:13]1[C:14]([CH3:15])=[N:8][N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:17]=1[CH3:18])=[O:20])[CH3:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7516PhenylhydrazineHCID 79063Ethyl 2-acetylacetoacetate

Product 1

HCID 6569643,5-Dimethyl-1-phenyl-1H-pyrazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Similar to Example 1, phenyl hydrazine (7.5 mmol, 0.8 g) and 2-acetyl-3-oxo-butyric acid ethyl ester (7.5 mmol, 1.3 g) were mixed in a solution of 50% pyridine in ethanol. The solvents were removed under vacuum and the oil resuspended in chloroform. The resulting suspension was washed with 5% sodium bicarbonate, 5% hydrochloric acid, and then brine. The organic layer was dried over NaSO4, the solids filtered, and the solvents removed under vacuum. The crude material was purified over silica gel to yield the named product as an oil. 1H-NMR (CDCl3, ppm): 1.37 t (3H); 2.51 s (6H); 4.32 q (2H); 7.42 bs (5H).

Workup

  1. customThe solvents were removed under vacuum
  2. washThe resulting suspension was washed with 5% sodium bicarbonate, 5% hydrochloric acid
  3. dry with materialThe organic layer was dried over NaSO4
  4. filtrationthe solids filtered
  5. customthe solvents removed under vacuum
  6. customThe crude material was purified over silica gel

Sources & evidence

ORD record
ord-32740fb7cd88475c80964fc430e15578
Source dataset
uspto-grants-2006_08
Patent number
US07087634B2

Linked notes

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