Triethylamine → 1-(6-Methoxy-3-pyridyl)-5-(3-methylphenyl)pyrazole-3-carboxylic acid ethyl ester

HRID 1437204Notes

Reaction equation

HRID 1437204 reaction equation
Cl.[NH:2]([C:4]1[CH:5]=[CH:6][C:7]([O:10][CH3:11])=[N:8][CH:9]=1)[NH2:3].C(N(CC)CC)C.[CH2:19]([O:21][C:22](=[O:35])[C:23](=O)[CH2:24][C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[CH:28]=1)=O)[CH3:20]>C(O)C>[CH2:19]([O:21][C:22]([C:23]1[CH:24]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[CH:28]=2)[N:2]([C:4]2[CH:9]=[N:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=2)[N:3]=1)=[O:35])[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 230902035-Hydrazinyl-2-methoxypyridine hydrochlorideHCID 45790297Ethyl 4-(3-methylphenyl)-2,4-dioxobutanoate

Product 1

HCID 579406821-(6-Methoxy-3-pyridyl)-5-(3-methylphenyl)pyrazole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Hydrazino-2-methoxypyridine hydrochloride (0.380 g) obtained from Referential Example 1 and triethylamine (0.30 mL) were added to a solution of the above-obtained 4-(3-methylphenyl)-2,4-dioxobutanoic acid ethyl ester (1.014 g) dissolved in ethanol (20 mL) at room temperature. The resultant mixture was refluxed under heat for 14 hours, and then cooled in air. The solvent was evaporated under reduced pressure, and the residue was partitioned between chloroform and water. The aqueous layer was extracted with chloroform. The organic layer was washed with saturated brine and dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography (hexane-ethyl acetate: 20%), to thereby give the title compound as an oily substance (0.451 g, 62%).

Workup

  1. temperatureunder heat for 14 hours
  2. temperaturecooled in air
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was partitioned between chloroform and water
  5. extractionThe aqueous layer was extracted with chloroform
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over sodium sulfate anhydrate
  8. filtrationfollowed by filtration
  9. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c2834f8fcf444137bf95f8230c2cd015
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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