Triethylamine → 1-Nicotinoyl-3-phenyl-2-pyrazoline

HRID 2307260

Reaction equation

HRID 2307260 reaction equation
[C:1]1([C:7]2[CH2:11][CH2:10][NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:13]([N:9]1[CH2:10][CH2:11][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8]1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 5897453-Phenyl-4,5-dihydro-1H-pyrazole

Product 1

HCID 98196571-Nicotinoyl-3-phenyl-2-pyrazolineYield 74.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Phenyl-2-pyrazoline (2.9 g) synthesized in Reference Example 2 was dissolved in chloroform (20 ml). Thereto were added nicotinic acid chloride hydrochloride (4 g) and triethylamine (6 ml) with ice-cooling. Stirring was conducted for 30 minutes at room temperature. The reaction mixture was washed with water and concentrated under vacuum. The residue was purified by silica gel column chromatography (methanol:chloroform=1/100) to obtain 3.7 g of a title compound.

Workup

  1. temperaturecooling
  2. washThe reaction mixture was washed with water
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by silica gel column chromatography (methanol:chloroform=1/100)

Sources & evidence

ORD record
ord-6893ebef7bf741d3bf85b5185d3d46de
Source dataset
uspto-grants-2004_12
Patent number
US06831083B2

Linked notes

Loading…